Name: 7580-85-0|Ethyleneglycolmono-tert-butylether|95%
Brand: Ambeed
SKU: A853205
Price: 36.0 USD
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Rating: 95 (35 reviews)

1
[ 75-21-8 ]
[ 75-65-0 ]
[ 7580-85-0 ]

Yield	Reaction Conditions	Operation in experiment
97.3%	With K-MgO/γ-alumina In tetrahydrofuran at 50℃; for 5h;	1-3 S2. Preparation of ethylene glycol mono-tert-butyl ether Add 8mol tert-butanol (592g) and 8g of K-MgO / γ-alumina solid base prepared in step S1 to the reaction kettle,After stirring well, after raising the temperature to 50 ,Slowly add 2L of 0.5moL / L ethylene oxide tetrahydrofuran solution dropwise. After the dropwise addition, keep the reaction for 5 hours.After the reaction, the solid base was removed by filtration,Distillation under reduced pressure gave 114.8 g of high-purity ethylene glycol mono-tert-butyl ether with a yield of 97.3% (calculated as ethylene oxide).
	With hydro silicate
	With hydro silicate

Reference： [1]Current Patent Assignee: Zhou Yuwen - CN110724039, 2020, A Location in patent: Paragraph 0021-0045
[2]Ashburn; Collett; Lazzell [Journal of the American Chemical Society, 1935, vol. 57, p. 1862]
[3]Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - GB354357, 1930, A Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - US1996003, 1931, A Current Patent Assignee: I.G.Farbenind. - DE558646, 1930 [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 156][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 156]

2
[ 507-19-7 ]
[ 107-21-1 ]
[ 7580-85-0 ]

Reference： [1]Kitano; Fukui [Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1955, vol. 58, p. 355][Chem.Abstr., 1956, p. 4063] Lewis; Susi [Journal of the American Chemical Society, 1952, vol. 74, p. 840]

3
[ 107-21-1 ]
[ 115-11-7 ]
[ 7580-85-0 ]
[ 26547-47-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride at 75℃;
	With sulfuric acid at 75℃;
	With hydrogenchloride at 75℃;

With sulfuric acid at 75℃;

Reference： [1]Evans; Edlund [Industrial and Engineering Chemistry, 1936, vol. 28, p. 1188]
[2]Evans; Edlund [Industrial and Engineering Chemistry, 1936, vol. 28, p. 1188]
[3]Current Patent Assignee: SHELL PLC - DE629601, 1932, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 103][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 103] Current Patent Assignee: SHELL PLC - US1968033, 1931, A
[4]Current Patent Assignee: SHELL PLC - DE629601, 1932, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 103][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 103] Current Patent Assignee: SHELL PLC - US1968033, 1931, A

4
[ 64-18-6 ]
[ 7580-85-0 ]
[ 74338-98-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	In water for 12h; Ambient temperature;

Reference： [1]Montanari, Fernando; Tundo, Pietro [Journal of Organic Chemistry, 1982, vol. 47, # 7, p. 1298 - 1302]

5
[ 7580-85-0 ]
[ 79-11-8 ]
[ 74338-99-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol for 2h; Heating;

Reference： [1]Montanari, Fernando; Tundo, Pietro [Journal of Organic Chemistry, 1982, vol. 47, # 7, p. 1298 - 1302]

6
[ 7580-85-0 ]
[ 98-59-9 ]
[ 108366-80-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In tetrahydrofuran; water at 0 - 5℃; for 2h;
90%	With sodium hydroxide In tetrahydrofuran
61%	With triethylamine In dichloromethane at 0 - 20℃; for 0.5h;	27.1 Step 1 2-(tert-butoxy) ethyl 4-methyl sulfonate 27b In 0 °C lower, the triethylamine (0.53 ml, 3 . 8mmol) and methyl chloride (291 mg, 1 . 53mmol) is added to the ethylene glycol butyl ether uncle Shan 27a (201 mg, 1 . 7mmol) of dichloromethane (20 ml) in solution, the reaction system for the reaction at room temperature 30 minutes. After the reaction, using 20 ml reaction material, extraction with methylene chloride (20 ml × 2). The combined organic phase is adjusted to for pH=7 saturated ammonium chloride aqueous solution, washing with water (20 ml × 2), saturated salt water washing (20 ml), anhydrous sodium sulfate for drying, filtering, the filtrate concentrated under reduced pressure, the residue is purified by silica gel column chromatography [petroleum ether/ethyl acetate (v/v)=3/1], to obtain title compound 27b (282 mg, colorless liquid), yield: 61.0%.

With triethylamine In dichloromethane at 0 - 20℃; for 17.5h;

9-1 Dissolve ethylene glycol mono-tert-butyl ether (2.62 g, 22.17 mmol) and triethylamine (3.36 g, 11.02 mmol) in 40 mL methylene chloride at 0°C. Dissolve para- TOLUENESULFONYL chloride (4.2277 g, 22.17 mmol) in 10 mL methylene chloride and add it dropwise to the reaction. After 30 minutes raise the reaction to room temperature and allow it to stir for 17 hours. Dilute the reaction with methylene chloride and wash it with water (1 X), 1 N HCL (1 X), saturated aqueous sodium hydrogen carbonate (IX) and brine (1X). Dry the organic layer with magnesium sulfate. Filter and remove the solvent in vacuo to give 4.6387 g of crude toluene-4-sulfonic acid 2-tert-butoxyethyl ester. Dissolve this crude material (1.2423 g, 4.56 mmol) and di-benzyl iminodicarboxylate (1.4385 g, 5.04 mmol) (see Synthesis, 1988,992-994) in 20 mL acetonitrile. Add potassium tert- butoxide (575.9 mg, 5.13 mmol) to the reaction mixture and heat it to reflux for 24 hours. Cool the reaction to room temperature and remove the solvent in vacuo. Dissolve the residue in methylene chloride and wash it with water (1X) and brine (1X). Dry the organic layer with magnesium sulfate. Filter and remove the solvent in vacuo to give 1. 9215 g of crude material. Purify via Biotage chromatography (EtOAc/Hexanes) to afford 387.8 mg of (2-tert-butoxyethyl) dicarbamic acid benzyl ester (22%). MS (ES): m/z 386.3 (M+H). Dissolve (2-tert-butoxyethyl) dicarbamic acid benzyl ester (387.8 mg, 1.01 mmol) and 5% Pd/C (0.212 g) in absolute ethanol and expose it to 60 psi OF H2 for 18 hours. Filter the reaction mixture over a pad of celite. Acidify the filtrate with 5N HCI and concentrate in vacuo to obtain 139.4 mg of a crude residue containing the HCI salt of 2- tert-butoxyethylamine. Dissolve this crude material (139.4 mg, 0.852 mmol) in 10 mL pyridine at 25°C. To this add 2-THIOACETYLISOINDOLE-1, 3-dione (180.53 mg, 0.88 mmol) and allow to stir for 23 hours. Concentrate the reaction mixture in vacuo and dissolve the residue in methylene chloride and wash it with 1 N HCI (1 X). Dry the organic layer with magnesium sulfate. Filter and remove the solvent in vacuo to give 266.9 mg of crude product. Triturate this crude material in diethyl ether and remove the solids by filtration. Concentrate the filtrate in vacuo to afford 176.2 mg of a crude solid. Purify via Biotage chromatography to afford 74.1 MG OF N- (2-TERT-BUTOXYETHYL) thioacetamide. Dissolve this thioacetamide (74.1 mg, 0.423 mmol) in 20 mL methylene chloride and add methyl TRIFLUOROMETHANESULFONATE (76.3 mg, 0.465 mmol). Allow the reaction mixture to stir for an additional 21 hours. Decant the diethyl ether from the oil and triturate the oil with diethyl ether (3X). Remove any excess diethyl ether from the oily residue in vacuo to obtain 60.3 mg of crude triflic acid salt OF N- (2-TERT-BUTOXYETHYL) thioacetimidic acid methyl ester as an oil. Dissolve this crude product (60.3 mg, 0.62. 5 mmol) in 10 mL pyridine and add N-(R)-(6-AMINO-2 (R)-HYDROXYINDAN-1-YL)-4-BROMOBENZAMIDE (62.5 mg, 0.180 mmol). Allow the reaction to stir at 25°C for 22 hours. Remove the solvent in vacuo and partition the residue between methylene chloride and saturated aqueous sodium hydrogen carbonate. Dry the organic layer with magnesium sulfate. Filter and remove the solvent IN VACUO to give 31.4 mg of crude product. Purify via Biotage chromatography (10% MeOH/EtOAc) to afford 6.6 mg of the titled product (8% yield). MS (ES): M/Z 488. 1 (M+H).

Reference： [1]Ouchi; Inoue; Liu; Nagamune; Nakamura; Wada; Hakushi [Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 4, p. 1260 - 1262]
[2]Ouchi, Mikio; Inoue, Yoshihisa; Wada, Kazuhito; Iketani, Shin-ichi; Hakushi, Tadao; Weber, Edwin [Journal of Organic Chemistry, 1987, vol. 52, # 12, p. 2420 - 2427]
[3]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN105461762, 2016, A Location in patent: Paragraph 0765; 0766; 0767; 0768
[4]Current Patent Assignee: ELI LILLY & CO - WO2004/94363, 2004, A1 Location in patent: Page 36-37

7
[ 42518-98-9 ]
[ 7580-85-0 ]
[ 91505-31-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In tetrahydrofuran 1) r.t., 1 h, 2) reflux, 10 min;

Reference： [1]Binder, Dieter; Pyerin, Michael; Pusterer, Friedrich [Monatshefte fur Chemie, 1999, vol. 130, # 5, p. 645 - 651]

8
[ 7580-85-0 ]
[ 91505-31-6 ]
[ 91505-34-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride In N,N-dimethyl-formamide at 65℃; for 1h;
62.27%	With sodium hydride In N,N-dimethyl-formamide at 20 - 65℃; for 1.5h; Inert atmosphere;	37B Intermediate 37B: 2-(tert-butoxy)ethyl 5-(2-(tert-butoxy)ethoxy) thiophene-2-carboxylate Sodium hydride (223 mg, 5.58 mmol, 60% purity) was added to a solution of 243 2-tert-butyloxyethyl alcohol (660 mg, 5.58 mmol) in 51 DMF (10.00 mL) at 20°C. Intermediate 37B (1.00 g, 3.72 mmol) was then added. The reaction solution was stirred at 20 to 65°C for 1.5h under nitrogen. After TLC showed the reaction finished, the mixture was quenched with 180 glacial acetic acid (1 mL), extracted with ethyl acetate (30 mL), washed with saturated sodium bicarbonate solution (30 mL) and saturated brine (30 mL*2), dried over anhydrous sodium sulfate, filtered and concertrated. The residue was purified by column chromatography to give the 246 title compound (813 mg, 62.27% yield) as white solid. LCMS (ESI) m/z: 345 (M+1). 1HNMR (400 MHz, CHLOROFORM-d) δ ppm 1.2-1.3 (m, 18 H), 3.6-3.7 (m, 2H), 3.71-3.76 (m, 2H), 4.17-4.26 (m, 2H), 4.30-4.39 (m, 2H), 6.27 (d, J=4.14 Hz, 1H), 7.55 (d, J=4.14 Hz, 1H).

Reference： [1]Binder, Dieter; Pyerin, Michael; Pusterer, Friedrich [Monatshefte fur Chemie, 1999, vol. 130, # 5, p. 645 - 651]
[2]Current Patent Assignee: HARBIN ZHENBAO PHARMACEUTICAL - EP3473628, 2019, A1 Location in patent: Paragraph 0229; 0231

9
[ 7580-85-0 ]
[ 76-05-1 ]
[ 480445-51-0 ]
8-(4-bromo-benzyl)-1-(2-hydroxy-ethyl)-3-isobutyl-3,7-dihydro-purine-2,6-dione; compound with trifluoro-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 8-(4-bromo-benzyl)-3-isobutyl-3,7-dihydro-purine-2,6-dione With {4-[(2,4-dimethoxyphenyl)chloromethyl]phenoxy}-Rink resin; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: tert-butyl glycidyl ether With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Stage #3: trifluoroacetic acid In dichloromethane at 20℃; for 1h;

Reference： [1]Beer, David; Bhalay, Gurdip; Dunstan, Andrew; Glen, Angela; Haberthuer, Sandra; Moser, Heinz [Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 15, p. 1973 - 1976]

10
[ 7580-85-0 ]
[ 124-63-0 ]
2-(tert-butoxy)ethyl methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In tert-butyl methyl ether at 0 - 20℃; for 2h;	1.1 Rawmaterial 1a (47g, 0.4mol. 1eq), Triethylamine(51.8g, 0.51mol, 1.28eq), ΜΤΒΕ (400ml) was added to a 1L reaction flask, ice-water bath Down to 0°C after dropping MsCl (50.4g, 0.44mol, 1.1eq). After dropping completes, the drops stirred at room temperature for 2 hours the reaction was stopped. The organic phase/layer washed with saturated NaHCO3, Washed with saturated brine then dried and concentrated to give the product (83.3g, 0.4mol) Yield 100%.
	With triethylamine In dichloromethane at 0℃; for 2h;
	With sodium hydrogencarbonate; triethylamine In dichloromethane	56 4-(1-(2-(t-Butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane PREPARATION 56 4-(1-(2-(t-Butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Combine 2-t-butoxyethanol (3.37 g, 28.5 mmol), triethylamine (6 mL, 43 mmol), and dichloromethane (150 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (2.9 mL,:37.5 mmol). After 3 days, dilute the reaction mixture with dichloromethane and extract with a saturated solution of sodium bicarbonate and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-(t-butoxy)ethyl mesylate: Rf=0.75 (silica gel, 50% ethyl acetate/hexane).

	With sodium hydrogencarbonate; triethylamine In dichloromethane	56 4-(1-(2-(t-Butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane PREPARATION 56 4-(1-(2-(t-Butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Combine 2-t-butoxyethanol (3.37 g, 28.5 mmol), triethylamine (6 mL, 43 mmol), and dichloromethane (150 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (2.9 mL, 37.5 mmol). After 3 days, dilute the reaction mixture with dichloromethane and extract with a saturated solution of sodium bicarbonate and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-(t-butoxy)ethyl mesylate: Rf=0.75 (silica gel, 50% ethyl acetate/hexane).
	With sodium hydrogencarbonate; triethylamine In dichloromethane	56 4-(1-(2-(t-Butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Preparation 56 4-(1-(2-(t-Butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Combine 2-t-butoxyethanol (3.37 g, 28.5 mmol), triethylamine (6 mL, 43 mmol), and dichloromethane (150 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (2.9 mL, 37.5 mmol). After 3 days, dilute the reaction mixture with dichloromethane and extract with a saturated solution of sodium bicarbonate and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-(t-butoxy)ethyl mesylate: Rf=0.75 (silica gel, 50% ethyl acetate/hexane).
	With sodium hydrogencarbonate; triethylamine In dichloromethane	35 Synthesis of 4-(1-(2-(t-butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepan PREPARATION 35 Synthesis of 4-(1-(2-(t-butoxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepan Combine 2-t-butoxyethanol (3.37 g, 28.5 mmol), triethylamine (6 mL, 43 mmol), and dichloromethane (150 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (2.9 mL, 37.5 mmol). After 3 days, dilute the reaction mixture with dichloromethane and extract with a saturated solution of sodium bicarbonate and then brine. Dry the organic layer over Na2 SO4, filter, and evaporate in vacuo to give 2-(t-butoxy)ethyl mesylate: Rf =0.75 (silica gel, 50% ethyl acetate/hexane).
	With triethylamine In tetrahydrofuran at 0 - 25℃; for 20h;	42.1 Step 1: To a solution of 2-(tert-butoxy)ethan-l-ol (1 g, 8.46 mmol) and TEA (3.54 mL, 25.4 mmol) in THF (15 mL) was added dropwise Ms-Cl (0.989 mL, 12.69 mmol) at 0 °C. The reaction mixture was stirred for 20 hours at 25 °C. TLC showed that SM was consumed completely. The reaction mixture was poured into water (20 mL), extracted by EtOAc (30 mL), washed with 1M HC1 (5 ml), sat NaHCCh, (10 ml) and brine (10 ml). The organic layer was dried over Na2S04, filtered and concentrated to give 2-(tert-butoxy)ethyl methanesulfonate (l .2g, 1.352 mmol, 15.98 % yield) as a brown oil which was used in the next step without purification.

Reference： [1]Current Patent Assignee: BEIJING LAVIANA PHARMATECH - CN103304356, 2016, B Location in patent: Paragraph 0148-0152
[2]Kim, Kyoung Soon; Kimball, S. David; Misra, Raj N.; Rawlins, David B.; Hunt, John T.; Xiao, Hai-Yun; Lu, Songfeng; Qian, Ligang; Han, Wen-Ching; Shan, Weifang; Mitt, Toomas; Cai, Zhen-Wei; Poss, Michael A.; Zhu, Hong; Sack, John S.; Tokarski, John S.; Chang, Chieh Ying; Pavletich, Nikola; Kamath, Amrita; Humphreys, William G.; Marathe, Punit; Bursuker, Isia; Kellar, Kristen A.; Roongta, Urvashi; Batorsky, Roberta; Mulheron, Janet G.; Bol, David; Fairchild, Craig R.; Lee, Francis Y.; Webster, Kevin R. [Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3905 - 3927]
[3]Current Patent Assignee: SANOFI - US2001/34343, 2001, A1
[4]Current Patent Assignee: Aventis Pharmaceuticals Inc. - US6423704, 2002, B1
[5]Current Patent Assignee: SANOFI - US6194406, 2001, B1
[6]Current Patent Assignee: SANOFI - US5932571, 1999, A
[7]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2020/3093, 2020, A1 Location in patent: Page/Page column 49

11
[ 33252-28-7 ]
[ 7580-85-0 ]
6-(2-tert-butoxy-ethoxy)-nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: tert-butyl glycidyl ether With lithium hexamethyldisilazane In tetrahydrofuran for 0.5h; Stage #2: 6-chloronicotinonitrile In tetrahydrofuran at 70℃; for 9h; Further stages.;

Reference： [1]Elliott, Richard L.; Oliver, Robert M.; Hammond, Marlys; Patterson, Terrell A.; She, Li; Hargrove, Diane M.; Martin, Kelly A.; Maurer, Tristan S.; Cory Kalvass, J. Cory; Morgan, Bradley P.; DaSilva-Jardine, Paul A.; Stevenson, Ralph W.; Mack, Christine M.; Cassella, James V. [Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 670 - 673]

12
[ 67-56-1 ]
[ 20212-13-9 ]
[ 7580-85-0 ]
1,3-diacetyl-2-imidazolone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,3-diacetyl-2,3-dihydro-1H-imidazol-2-one; tert-butyl glycidyl ether With N-Bromosuccinimide In 1,4-dioxane Stage #2: methanol With caesium carbonate; triethylamine

Reference： [1]Ishizuka, Tadao; Katahira, Tomokazu; Seo, Ryushi; Matsunaga, Hirofumi; Kunieda, Takehisa [Tetrahedron Letters, 2004, vol. 45, # 51, p. 9327 - 9330]

13
[ 1012073-06-1 ]
[ 7580-85-0 ]
C₁₁H₁₉N₃O₃S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 2h;	222 Example 222; In 2 ml of tetrahydrofuran were dissolved 340 mg of the compound represented by the formula (IIa-1) and 200 mg of 2- (tert-butoxy) ethanol, 70 mg of sodium hydride (60% oily) and 0.5 ml of tetrahydrofuran were added under ice- cooling, and the mixture was stirred at room temperature for 2 hours. Thereafter, an aqueous saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with t-butyl methyl ether. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel preparative thin layer chromatography to obtain 400mg of a compound represented by the formula (222) : (hereinafter, referred to as present compound (222)). 1H-NMR (CDCl3, TMS) δ (ppm) : 4.64-4.61 (2H, m) , 3.74-3.72 (2H, TCL), 3.04 (6H, br), 1.21 (9H, s)

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - WO2008/32858, 2008, A2 Location in patent: Page/Page column 271-272

14
[ 7580-85-0 ]
[ 28047-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine-SO₃ complex; triethylamine In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 6.83333h;	16.16a 16a) (1,1-Dimethylethyl)oxyethanal oxime To a stirring solution of ethylene glycol tert-butyl ether (27.5 mL, 209 mmol) and triethylamine (87.5 mL, 628 mmol) in dichloromethane (600 mL) at 0° C. was added, over a period of approximately 45 minutes, a solution of sulfur trioxide-pyridine complex (100 g, 628 mmol) in dimethylsulfoxide (600 mL) that had been stirring for approximately 25 minutes. The mixture was allowed to warm to ambient temperature and stir over 6 hours and was then poured into ether, washed three times with 10% aqueous citric acid, then brine and was concentrated. The residue was taken up with ethanol (2.65 L) and filtered into a stirring solution of hydroxylamine hydrochloride (16.0 g, 230 mmol) and sodium hydroxide (9.20 g, 230 mmol) in water (125 mL). The solution was heated to approximately 90° C. and stirred for approximately 17 hours. The mixture was then concentrated and the residue was taken up with ethyl acetate and washed twice with water containing sodium chloride. The combined aqueous layers were back-extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 15% ethyl acetate in hexanes) to afford 1,1-dimethylethyl)oxyethanal oxime (8.59 g, 31%). 1H-NMR (400 MHz, DMSO-d6) δ 11.02 (s, 0.5H), 10.73 (s, 0.5H), 7.25 (t, J=6 Hz, 0.5H), 6.67 (t, J=4 Hz, 0.5H), 4.11 (d, J=4 Hz, 1H), 3.89 (d, J=6 Hz, 1H), 1.12 (s, 9H).
	With Dess-Martin periodane In dichloromethane at 20℃; for 0.166667h;
	With sulfur trioxide pyridine complex; triethylamine In dichloromethane; dimethyl sulfoxide at 0 - 20℃;	1.a To a stirring solution of ethylene glycol tert-butyi ether (27.5 rnL, 209 mmol) and triethylamine (87.5 mL, 628 mmol) in dichloromethane (600 mL) at 0 0C was added, over a period of approximately 45 minutes, a solution of sulfur trioxide-pyridine complex (100 g, 628 mmol) in dimethylsulfoxide (600 mL) that had been stirring for approximately 25 minutes. The mixture was allowed to warm to ambient temperature and stir over 6 hours and was then poured into ether, washed three times with 10% aqueous citric acid, then brine and concentrated. The residue was taken up with ethanol (2.65 L) and filtered into a stirring solution of hydroxylamine hydrochloride (16.0 g, 230 mmol) and sodium hydroxide (9.20 g, 230 mmol) in water (125 mL). The solution was heated to approximately 90 0C and stirred for approximately 17 hours. The mixture was then concentrated and the residue was taken up with ethyl acetate and washed twice with water containing sodium chloride. The combined aqueous layers were back-extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 15% ethyl acetate in hexanes) to afford 1,1- dimethylethyl)oxyethanal oxime (8.59 g, 31%). 1H-NMR (400 MHz, DMSO-J6) δ 11.02 (s, 0.5H), 10.73 (s, 0.5H), 7.25 (t, J = 6 Hz, 0.5H ), 6.67 (t, J = 4 Hz, 0.5H), 4.11 (d, J = 4 Hz, IH), 3.89 (d, J = 6 Hz, IH), 1.12 (s, 9H).

	With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine In dichloromethane at 0 - 20℃;
	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate Reflux;
8.47 g	With sulfur trioxide pyridine complex; triethylamine In dichloromethane; dimethyl sulfoxide at 0 - 20℃; Inert atmosphere;	tert-butoxyacetaldehyde Sulfur trioxide pyridine complex (40.4 g, 254 mmol) in 250 ml_ of dimethyl sulfoxide was added to 2-tert-butoxyethanol (CAS 7580-85-0, 1 1 ml_, 85 mmol) and triethylamine (35 ml_, 250 mmol) dissolved in 240 mL of dichloromethane at 0 °C over 45 minutes. The reaction mixture was then warmed to room temperature and stirred overnight under argon. The reaction mixture was diluted with diethyl ether and washed with 10% aqueous citric acid followed by brine. The organic phase was dried over magnesium sulfate, passed through a plug of silica and the solvent was removed under reduced pressure to give 8.47 g of the title compound, which was taken to the next step without further purification.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2008/96921, 2008, A1 Location in patent: Page/Page column 57
[2]Yang, Zhi-Qiang; Barrow, James C.; Snipe, William D.; Schlegel, Kelly-Ann S.; Shu, Youheng; Yang, F. Vivien; Lindsley, Craig W.; Rittle, Kenneth E.; Bock, Mark G.; Hartman, George D.; Uebele, Victor N.; Nuss, Cindy E.; Fox, Steve V.; Kraus, Richard L.; Doran, Scott M.; Connolly, Thomas M.; Tang, Cuyue; Ballard, Jeanine E.; Kuo, Yuhsin; Adarayan, Emily D.; Prueksaritanont, Thomayant; Zrada, Matthew M.; Marino, Michael J.; Graufelds, Valerie Kuzmick; DiLella, Anthony G.; Reynolds, Ian J.; Vargas, Hugo M.; Bunting, Patricia B.; Woltmann, Richard F.; Magee, Michael M.; Koblan, Kenneth S.; Renger, John J. [Journal of Medicinal Chemistry, 2008, vol. 51, # 20, p. 6471 - 6477]
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2009/5998, 2009, A1 Location in patent: Page/Page column 87
[4]Location in patent: scheme or table Bass, Jonathan Y.; Caldwell, Richard D.; Caravella, Justin A.; Chen, Lihong; Creech, Katrina L.; Deaton, David N.; Madauss, Kevin P.; Marr, Harry B.; McFadyen, Robert B.; Miller, Aaron B.; Parks, Derek J.; Todd, Dan; Williams, Shawn P.; Wisely, G. Bruce [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 2969 - 2973]
[5]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]
[6]Current Patent Assignee: BAYER AG - WO2019/96907, 2019, A1 Location in patent: Page/Page column 224-225

15
[ 7580-85-0 ]
3-{2-[6-(2-tert-butoxyethoxy)pyridin-3-yl]-1H-imidazol-4-yl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium bistrimethylsilylamide / tetrahydrofuran / 0.5 h 1.2: 87 percent / tetrahydrofuran / 9 h / 70 °C 2.1: lithium bistrimethylsilylamide / tetrahydrofuran / 19 h / 20 °C 2.2: aq. NaHCO₃; K₂CO₃ / tetrahydrofuran; CHCl₃ 2.3: tetrahydrofuran; CHCl₃ / 22 h

Reference： [1]Elliott, Richard L.; Oliver, Robert M.; Hammond, Marlys; Patterson, Terrell A.; She, Li; Hargrove, Diane M.; Martin, Kelly A.; Maurer, Tristan S.; Cory Kalvass, J. Cory; Morgan, Bradley P.; DaSilva-Jardine, Paul A.; Stevenson, Ralph W.; Mack, Christine M.; Cassella, James V. [Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 670 - 673]

16
[ 7580-85-0 ]
[ 91505-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / NEt₃ / tetrahydrofuran / 1) r.t., 1 h, 2) reflux, 10 min 2: 65 percent / NaH / dimethylformamide / 1 h / 65 °C 3: 93 percent / methanol / 1 h / Heating
	Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 2 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 - 65 °C / Inert atmosphere 3.1: 1 h / 65 °C / Inert atmosphere

Reference： [1]Binder, Dieter; Pyerin, Michael; Pusterer, Friedrich [Monatshefte fur Chemie, 1999, vol. 130, # 5, p. 645 - 651]
[2]Current Patent Assignee: HARBIN ZHENBAO PHARMACEUTICAL - EP3473628, 2019, A1

17
[ 7580-85-0 ]
[ 91505-34-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / NEt₃ / tetrahydrofuran / 1) r.t., 1 h, 2) reflux, 10 min 2: 65 percent / NaH / dimethylformamide / 1 h / 65 °C
	Multi-step reaction with 2 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 2 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 20 - 65 °C / Inert atmosphere

Reference： [1]Binder, Dieter; Pyerin, Michael; Pusterer, Friedrich [Monatshefte fur Chemie, 1999, vol. 130, # 5, p. 645 - 651]
[2]Current Patent Assignee: HARBIN ZHENBAO PHARMACEUTICAL - EP3473628, 2019, A1

18
[ 7580-85-0 ]
[ 108366-72-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / aq. NaOH / tetrahydrofuran 2: 1.) NaOH / 1.) THF, 66 deg C, 1 h, 2.) THF, 66 deg C, 24 h

Reference： [1]Ouchi, Mikio; Inoue, Yoshihisa; Wada, Kazuhito; Iketani, Shin-ichi; Hakushi, Tadao; Weber, Edwin [Journal of Organic Chemistry, 1987, vol. 52, # 12, p. 2420 - 2427]

19
[ 7580-85-0 ]
[ 74339-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium tert-butoxide / 2-methyl-propan-2-ol / 2 h / Heating 2: oxalyl chloride, pyridine / benzene / 10 h / Ambient temperature 3: 66 percent / Et₃N / benzene / 8 h

Reference： [1]Montanari, Fernando; Tundo, Pietro [Journal of Organic Chemistry, 1982, vol. 47, # 7, p. 1298 - 1302]

20
[ 7580-85-0 ]
[ 74339-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium tert-butoxide / 2-methyl-propan-2-ol / 2 h / Heating 2: 60 percent / p-toluenesulfonic acid / benzene / 4 h / Heating 3: 90 percent / LiAlH₄ / tetrahydrofuran / Heating

Reference： [1]Montanari, Fernando; Tundo, Pietro [Journal of Organic Chemistry, 1982, vol. 47, # 7, p. 1298 - 1302]

21
[ 7580-85-0 ]
[ 74339-01-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium tert-butoxide / 2-methyl-propan-2-ol / 2 h / Heating 2: oxalyl chloride, pyridine / benzene / 10 h / Ambient temperature

Reference： [1]Montanari, Fernando; Tundo, Pietro [Journal of Organic Chemistry, 1982, vol. 47, # 7, p. 1298 - 1302]

22
[ 7580-85-0 ]
[ 80515-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium tert-butoxide / 2-methyl-propan-2-ol / 2 h / Heating 2: 60 percent / p-toluenesulfonic acid / benzene / 4 h / Heating

Reference： [1]Montanari, Fernando; Tundo, Pietro [Journal of Organic Chemistry, 1982, vol. 47, # 7, p. 1298 - 1302]

23
[ 7580-85-0 ]
[ 177787-26-7 ]
[ 570407-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dmap at 0 - 20℃;	98 Reference Example 98 To a solution of 1.52 g of 3,4,5-trifluorobenzoic acid in 15 ml of dichloromethane, 0.92 ml of oxalyl chloride was added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes and at room temperature for 80 minutes. After DMF was added dropwise, the mixture was stirred at room temperature for 1 hour. To the residue obtained by the evaporation of the solvent under reduced pressure, 20 ml of pyridine, 3.40 ml of 2-tert-butoxyethanol, and 1 fold by spatula of DMAP were added 'under ice cooling, and the mixture was stirred at room temperature overnight. After the evaporation of the solvent under reduced pressure, the residue was mixed with saturated NaHCO3 aq. extracted with EtOAc, washed with water and brine, and dried over MgSO4. The solvent was evaporated under reduced pressure to obtain 2.10 g of crude 3,4,5-trifluorobenzoic acid 2-tert-butoxyethyl ester. To a solution of 1.03 g of potassium tert-butoxide in 15 ml of THF, 1.50 ml of 2-tert-butoxyethanol was added, and the mixture was stirred for 40 minutes. The reaction solution was cooled to -78 °C, a solution of 2.10 g of crude 3,4,5-trifluorobenzoic acid 2-tert-butoxyethylester in 5 ml of THF was added thereto, and the mixture was stirred under ice cooling for 1 hour and at room temperature for 30 minutes. The reaction solution was mixed with saturated aqueous ammonium chloride, extracted with EtOAc, and washed with water and brine, and then dried over MgSO4. The residue obtained by the evaporation of the solvent under reduced pressure was purified by silica gel column chromatography (eluent: hexane-EtOAc = 100:1∼20:1) to obtain 2.24 g of 4-(2-tert-butoxyethoxy)-3,5-difluorobenzoic acid 2-tert-butoxyethyl ester.

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - EP1466912, 2004, A1 Location in patent: Page 22

24
[ 872625-38-2 ]
[ 7580-85-0 ]
(S)-9-{(3,5-bis-trifluoromethyl-benzyl)-[2-(2-tert-butoxy-ethyl)-2H-tetrazol-5-yl]-amino}-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 12h;	75.1 Example 75; Synthesis of (S)-5-(9-{(3,5-Bis-trifluoromethyl-benzyl)-[2-(2-hydroxy-ethyl)-2H-tetrazol-5-yl]-amino}-l,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-3,3-dimethyl-pentanoic acid; Step 1; Preparation of (S)-9-{(3,5-Bis-trifluoromethyl-benzyl)-[2-(2-tert-butoxy-ethyl)-2H-tetrazol-5-yl]-amino}-l,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester; To a solution of (S)-9-[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester(Example 73, Step 6) (0.167 mmol) in dichloromethane (20 mL), add 2-tert-butoxy-ethanol (0.835 mmol) and triphenylphosphine (0.501 mmol). To this solution, add diethylazodicarboxylate (0.501 mmol) dropwise at room temperature. After stirring for 12 h,remove the solvent under vacuum. Chromatograph the intermediate over silica gel,eluting with ethyl acetate/hexane (2 - 35 %) to afford the title compound as an oil.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2006/2342, 2006, A1 Location in patent: Page/Page column 144-145

25
[ 626-05-1 ]
[ 7580-85-0 ]
[ 312932-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; mineral oil	126 2-[2-(tert-butoxy)ethoxy]-6-bromopyridine Preparation 126 2-[2-(tert-butoxy)ethoxy]-6-bromopyridine Sodium hydride (6.8 g, 60% dispersion in mineral oil, 0.169 mol) was added portionwise to an ice-cold solution of 2-(tert-butoxy)ethanol (20.0 g, 0.169 mol) in toluene (500 ml) under nitrogen, and the solution stirred for 30 minutes whilst warming to ambient temperature. 2,6-Dibromopyridine (40.0, 0.169 mol) was added, and the reaction heated under reflux for 3 hours. The mixture was allowed to cool to ambient temperature and was diluted with water (100 ml), and extracted with ethyl acetate (2*400 ml). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow oil (quantitative). 1H nmr (CDCl3, 400 MHz) δ: 1.21 (s, 9H), 3.67 (t, 2H), 4.40 (t, 2H), 6.68 (d, 1H), 7.05 (d, 1H), 7.38 (t, 1H). LRMS: m/z 296/298 (M+23)+.
	In toluene; mineral oil	126 2-[2-(tert-butoxy)ethoxy]-6-bromopyridine Preparation 126 2-[2-(tert-butoxy)ethoxy]-6-bromopyridine Sodium hydride (6.8 g, 60% dispersion in mineral oil, 0.169 mol) was added portionwise to an ice-cold solution of 2-(tert-butoxy)ethanol (20.0 g, 0.169 mol) in toluene (500 ml) under nitrogen, and the solution stirred for 30 minutes whilst warming to ambient temperature. 2,6-Dibromopyridine (40.0, 0.169 mol) was added, and the reaction heated under reflux for 3 hours. The mixture was allowed to cool to ambient temperature and was diluted with water (1000 ml), and extracted with ethyl acetate (2*400 ml). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow oil (quantitative). 1H nmr (CDCl3, 400 MHz) δ:1.21 (s, 9H), 3.67 (t, 2H), 4.40 (t, 2H), 6.68 (d, 1H), 7.05 (d, 1H), 7.38 (t, 1H). LRMS: m/z 296/298 (M+23)+.

Reference： [1]Current Patent Assignee: PFIZER INC - US6511993, 2003, B1
[2]Current Patent Assignee: XEROX CORP - US2003/199440, 2003, A1

26
[ 7580-85-0 ]
[ 7693-46-1 ]
[ 220389-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In tetrahydrofuran; acetonitrile	7.1 Step 1 Step 1 2-t-Butoxyethyl-(4-nitrophenyl)carbonate A THF:acetonitrile (7:1, 10 mL) solution of 4-nitrophenyl chloroformate (6.71 mmol) was added to a THF:acetonitrile (7:1, 20 mL) solution of commercially available ethylene glycol mono-t-butyl ether (6.64 mmol) at 25° C. and then stirred for 0.25 hour. Pyridine (6.71 mmol) was then added dropwise over 4 minutes. Stirring was continued for 2 hours at 25° C. and then the reaction was diluted with ethyl acetate and washed with water, a saturated sodium chloride solution, dried with sodium sulfate and then evaporated to provide the title compound. 1H-NMR (CDCl3): δ 8.3 (d, 2H); 7.4 (d, 2H); 4.4 (t, 2H); 3.65 (t, 2H); 1.2 (s, 9H).
	With pyridine In dichloromethane	II.40 2-t-Butoxyethyl(4-nitrophenyl)carbonate Example II-40 2-t-Butoxyethyl(4-nitrophenyl)carbonate In 16 ml of methylene chloride was dissolved 1.77 g (15.0 mmol) of 2-t-butoxyethanol, 1.31 g (16.5 mmol) of pyridine was added to the solution, and under ice-cooling, 15 ml of a methylene chloride solution containing 3.12 g (15.0 mmol) of 4-nitrophenylchloroformate was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for 7 hours. The resulting reaction mixture was washed successively with water, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous saline solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by the silica gel column chromatography method (eluent: chloroform) to obtain 4.19 g (14.8 mmol) of the title compound as pale yellowish oily product. 1H-NMR (CDCl3) δ; 8.28 (d, J=8.8 Hz, 2H), 7.38 (d, J=8.8 Hz, 2H), 4.39 (t, J=5.1 Hz, 2H), 3.67 (t, J=5.1 Hz, 2H), 1.24 (s, 9H). CI-MS (m/z); 284

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6355643, 2002, B1
[2]Current Patent Assignee: UBE INDUSTRIES LIMITED - US6265418, 2001, B1

27
[ 335349-57-0 ]
[ 7580-85-0 ]
[ 335349-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In dimethyl sulfoxide;	Example E6 5-(2-tert.-Butoxy-ethoxy)-4-iodo-2-nitro-phenylamine Prepared from <strong>[335349-57-0]5-chloro-4-iodo-2-nitro-phenylamine</strong> (Example A1) (14.9 g, 50 mmol), 2-tert.-butoxyethanol (29.5 g, 250 mmol) and KOH (3.99 g, 60 mmol) in DMSO (25 mL) at 23 C. according to the general procedure E. Obtained as a yellow solid (14.3 g). MS (ISP) 381 [(M+H)+]; mp 144-146 C.

Reference： [1]Patent: US6407094,2002,B1

28
(R*,R*)-5-(2-((2-(3-chlorophenyl)-2-hydroxyethyl)amino)propyl)-1,3-benzodioxole-2,2-dicarboxylic acid [ No CAS ]
[ 7580-85-0 ]
5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(2-tert-butoxy-ethyl)-ester [ No CAS ]
[ 199669-57-3 ]

Yield	Reaction Conditions	Operation in experiment
100 mg (7%)	With toluene-4-sulfonic acid	6 5-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(2-tert-butoxy-ethyl) ester and 5-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid (2-tert-butoxy-ethyl) ester EXAMPLE 6 AND EXAMPLE 7 5-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(2-tert-butoxy-ethyl) ester and 5-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid (2-tert-butoxy-ethyl) ester To a stirred mixture of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid (1.0 g, 2.37 mmol), and 2-t-butoxy-1-ethanol (10 mL) was added p-toluenesulfonic acid (451 mg, 2.37 mmol). The mixture became homogeneous and was stirred at 23° C. After 12 h, an additional portion of p-toluenesulfonic acid (351 mg, 1.84 mmol) was added. After a total of 90 h, the solution was concentrated, and chromatographed on silica gel, eluding with CHCl3/MeOH (1/0, then 40/1, 20/1 and 10/1) to give 100 mg (7%) of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(2-tert-butoxy-ethyl) ester (Rf =0.25 (10/1 CHCl3 /MeOH)) as a yellow oil and 320 mg (26%) of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid (2-tert-butoxy-ethyl) ester (Rf =0.09 (10/1 CHCl3 /MeOH)) as an off-white solid.

Reference： [1]Current Patent Assignee: PFIZER INC - US5914339, 1999, A

29
[ 63676-19-7 ]
[ 7580-85-0 ]
[ 1972-28-7 ]
[ 220655-20-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triphenylphosphine In tetrahydrofuran	1 [6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thiophen-3-yl][(4-t-Butoxyethoxy)phenyl]methanone STR7 Example 1 [6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thiophen-3-yl][(4-t-Butoxyethoxy)phenyl]methanone STR7 To a mixture of [6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl](4-hydroxyphenyl)methanone (1.0 g, 2.6 mmol), ethylene glycol mono t-butyl ether (0.6 g. 5 mmol), and triphenylphosphine (1.02 g, 3.9 mmol) stirring in tetrahydrofuran (40 mL) at 0° C. was added diethyl azodicarboxylate (0.61 mL, 3.9 mmol) dropwise over a 10 minute period. After 2 hours at room temperature, the reaction was concentrated and the resulting residue purified by flash chromatography (silica gel, 3:1 hexanes/ethyl acetate) to give 1.37 g of the title compound as a thick syrup. Yield: 94%.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US6090843, 2000, A

30
[ 20697-04-5 ]
[ 7580-85-0 ]
1-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethyl acetate	P.6.1 PRODUCTION EXAMPLE 6 (1) 5.1 g of potassium tert-butoxide was added to 105 ml of ethylene glycol mono-tert-butyl ether. The mixture was heated to 80° C. Thereto was dropwise added 35.0 g of 2-(3-chlorophenyl)oxirane over 1 hour. The mixture was stirred for 2 hours at the same temperature. The reaction mixture was added to a mixture of 100 ml of ice water and 100 ml of ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to further distillation under reduced pressure to obtain 37.7 g of colorless oily 1-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethanol having a boiling point of 140°-146° C./0.9 mmHg.

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - US5280032, 1994, A

31
[ 75-21-8 ]
[ 64-17-5 ]
[ 67-63-0 ]
[ 75-65-0 ]
[ 110-80-5 ]
[ 109-59-1 ]
[ 7580-85-0 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 30℃; for 0.166667h;	8-10 Propylene oxide (4g) was added to an equimolar mixture of tert-butanol (0.2 mol, 14.8g), iso-propanol(12.0 g, 0.2 mol) and ethanol (0.2 mol, 9.2 g) . Then 0.1 ml of trimethyl borate was added and 0.3 ml of 48% aqueous HF. The reaction started immediately. After the consumption of the propylene oxide (30 min) the mixture was analyzed with GLC to show a mixture comprising mono- propoxylated derivatives of tert butanol, isopropanol and ethanol.

Reference： [1]Current Patent Assignee: SHELL PLC - WO2006/34997, 2006, A1 Location in patent: Page/Page column 19-20

32
[ 42518-98-9 ]
[ 7580-85-0 ]
[ 91505-16-7 ]

Yield	Reaction Conditions	Operation in experiment
42,3 g (80%)	With triethylamine In tetrahydrofuran	1 [2-(2-Methyl-2-propoxy)-1-ethyl]-ester of 5-chlorothiophene-2-carboxylic acid [2-(2-Methyl-2-propoxy)-1-ethyl]-ester of 5-chlorothiophene-2-carboxylic acid 36,2 g (0,2 mol) of 5-chlorothiophene-2-carboxylic acid chloride were dropped rapidly under stirring to a mixture consisting of 26,0 g (0,22 mol) of 2-tert.-butoxyethanol, 22,22 g (0,22 mol) of triethylamine in 100 ml of absolute THF at room temperature. Then it was stirred for 1 hour at room temperature and for 10 minutes at boiling temperature. After cooling it was evaporated in vacuo, the residue was partitioned between ether and NaHCO3 -solution, the organic phase was dried und evaporated in vacuo and then distilled in vacuo. Yield of crude material 50,3 g (96%), yield 42,3 g (80%) of a colorless oil, b.p. 90°-93° C./0,007 mbar.

Reference： [1]Current Patent Assignee: FRESENIUS SE & CO. KGAA - US4590203, 1986, A

33
[ 1343-93-7 ]
[ 115-11-7 ]
[ 7580-85-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethylene glycol	1 Synthesis of Ethylene Glycol Mono-t-Butyl Ether EXAMPLE 1 Synthesis of Ethylene Glycol Mono-t-Butyl Ether To a 300 cc pressure reactor fitted with heating, mixing and temperature controls was charged a mixture of ethylene glycol (62.0g, 1.0 mole) and 12-tungstophosphoric acid (5.0g). The reactor was flushed with nitrogen and pressured with isobutylene (28.0g, 0.5 mole), then heated to 120°C with mixing. After 4 hours at temperature, the reactor was cooled and the product (92.5g) recovered as a water-white liquid. Analysis by GC and GC-IR showed the presence of: Ethylene glycol conversion is 64%. Ethylene glycol mono-t-butyl ether selectivity is 73%.

Reference： [1]Current Patent Assignee: HUNTSMAN CORP - EP419077, 1991, A2

34
[ 7580-85-0 ]
[ 478010-54-7 ]
[ 918444-85-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydride In tetrahydrofuran at 0℃; for 0.25h;	34 Sodium hydride (91 mg, 2.3 mmol) was added to a cooled (0 0C) solution of 2- chloro-4,6-dimethoxy-5-nitropyrimidine (Intermediate 13; 0.5 g, 2.3 mmol) and ethylene glycol mono-tert butyl ether in anhydrous THF (10 ml) and the solution was stirred for 15 minutes. The mixture was divided between water(20 ml) and ethyl acetate (20 ml). The layers were separated, the organic layer was dried (MgSO4) and the solvent was removed. The crude product was then purified by column chromatography (SiO2; 4:1 light petroleum-ethyl acetate) to afford the title compound as an off-white solid (335 mg, 50 %). 1HNMR δ 4.49 (2 H, t), 4.06 (6 H, s), 3.73 (2 H, t) and 1.22 (9 H, s).
	With sodium hydride In tetrahydrofuran at -41℃;

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2007/582, 2007, A1 Location in patent: Page/Page column 59
[2]Olberg, Dag Erlend; Andressen, Kjetil Wessel; Levy, Finn Olav; Klaveness, Jo; Haraldsen, Ira; Sutcliffe, Julie L. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1846 - 1850]

35
[ 5469-69-2 ]
[ 7580-85-0 ]
[ 1177269-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl glycidyl ether With sodium hydride In 1,2-dimethoxyethane Stage #2: 6-chloro-pyridazin-3-ylamine In 1,2-dimethoxyethane at 90 - 130℃;	6-({2-[(1,1-dimethylethyl)oxy]ethyl}oxy)-3-pyridazinamine 6-({2-[(1,1-dimethylethyl)oxy]ethyl}oxy)-3-pyridazinamine 60% sodium hydride in mineral oil (102 mg, 2.54 mmol) was washed with anhydrous hexane (3 ml) and then suspended in DME (1 ml). A solution of 2-[(1,1-dimethylethyl)oxy]ethanol (200 mg, 1.692 mmol) in DME (2 ml) was added dropwise to the stirred suspension of NaH. After addition and hydrogen liberation was complete, the torbid mixture was taken up in a syringe and filtered through a millipore syringe filter into a screw-topped vial to give a limpid solution. 6-chloro-3-pyridazinamine (175 mg, 1.354 mmol) was added and the mixture was heated to 130° C. for 45 mins. The temperature was lowered to 90° C. and left overnight at this temperature, then heated again to 130° C. for 3 hours. The reaction mixture was cooled and neutralised with dilute hydrochloric acid solution (~2 ml, 1.0M). The reaction mixture was loaded onto a pre-conditioned SCX cartridge (20 g) and eluted with MeOH and then 2M NH3 in MeOH. The basic fractions containing product were evaporated and the residue was purified by reverse phase chromatography on the Biotage (eluent MeCN/water/formic acid 5/94.9/0.1, SNAP 60g C18 column). The fractions containing the desired product were loaded onto a pre-conditioned SCX cartridge (10 g) and eluted with MeOH and then 2M NH3 in MeOH. The basic fractions containing product were evaporated to give 90 mg of a yellow oil. 1H NMR (400 MHz, CDCl3): δ 6.89 (d, 1H), 6.80 (d, 1H), 4.51 (t, 2H), 4.47 (brs, 2H), 3.75 (t, 2H), 1.24 (s, 9H); UPLC-MS: 0.53 min, 212 [M+H]+ and 156 [M-butene+H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/203705, 2009, A1 Location in patent: Page/Page column 38

36
[ 7580-85-0 ]
[ 1173068-83-1 ]
[ 1173068-84-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(l) iodide; 1,10-Phenanthroline In toluene at 120℃; for 40h;	5 [00327] tert-Butyl 4-(3-iodo-l-(4-methoxybenzyl)-l H-pyrazolo [3, 4-b]pyridin-4- yl)piperazine-l-carboxylate (0.12 g, 0.218 mmol), Cu(I)I (0.0416 g, 0.218 mmol), 1,10- phenanthroline (0.0394 g, 0.218 mmol), 2-tert-butoxyethanol (0.774 g, 6.55 mmol) and KF on Al2O3 (40%; 0.222 g, 1.53 mmol) in toluene (4 mL) were stirred at 1200C for 40 hours. The reaction was then cooled to room temperature. Ethyl acetate (10 mL) was then added. The reaction was filtered through a pad of celite and concentrated to dryness. The resulting residue was purified by chromatography (hexane: ethyl acetate, 3:1) to give tert-butyl 4-(3-(2-tert- butoxyethoxy)- 1 -(4-methoxybenzyl)- 1 H-pyrazolo [3 ,4-b]pyridin-4-yl)piperazine- 1 -carboxylate (0.080 g, 68%) as a solid. MS APCI (+) m/z 540.5 detected.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2009/89359, 2009, A1 Location in patent: Page/Page column 75

37
[ 7580-85-0 ]
[ 150728-13-5 ]
[ 1177447-87-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; In toluene; at 55℃; for 2h;	Process for conversion of compound (1) to (2) (stage 1)Sodium hydroxide (1 eq) was added to ethylene glycol mono tert-butyl ether (3 eq) in toluene (7 vol). Compound (1) (1 eq) was added and the reaction mixture heated at 55C for 2 hours. After completion of the reaction, the mixture was acidified with a 1:1 mixture of concentrated HCl and water (0.4 vol) to pH 2. The organic layer was separated and washed with water (5 vol). The toluene was distilled off at 400C under vacuum (lOmbar) and the product (compound (2)) was obtained as a light brown solid (molar yield = 90%).
	With potassium carbonate;tetrabutylammomium bromide; In toluene; at 100 - 110℃; for 9h;	Example 1; Preparation of 4-(2-terf-Butoxyethoxy)-5-(2-methoxyphenoxy)-6-chloro-2,2'- bipyrimidine; 4,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine (50 gm), ethylene glycol mono-tert- butyl ether (18.4 gm), anhydrous powdered potassium carbonate (30.9 gm), tetra- butylammonium bromide (33.5 gm) and toluene (500 ml) were taken into a reaction flask and the resulting mixture was refluxed (100-HO0C) for 9 hours. After completion of the reaction, toluene was distilled out completely under reduced pressure. Methylene chloride (100 ml) and water (50 ml) were added to the residue, the resulting two layers were separated and the organic layer was washed with water (50 ml). The organic layer was dried over anhydrous sodium sulfate (10 gm) and distilled out methylene chloride under vacuum at 30-35C. After completion of distillation, isopropyl alcohol (75 ml) was added to the residue and cooled to 0- 50C. The resulting solid was filtered and dried at 600C to yield 36 gm of 4-(2-tert- butoxyethoxy)-5-(2-methoxyphenoxy)-6-chloro-2,2'-bipyrimidine (Purity by HPLC: 97%).

Reference： [1]Patent: WO2009/98517,2009,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2009/112954,2009,A2 .Location in patent: Example 1

38
[ 7580-85-0 ]
[ 1196073-28-5 ]
[ 1196073-23-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred suspension of sodium hydride (60% in mineral oil, 85 mg, 2.14 mmol) in DMF (4 mL) was added, dropwise, ethyleneglycol mono t-butyl ether (278 mg, 2.35 mmol). the reaction mixture was stirred for 25 min. A solution of 4,6-dichloro-2-methyl- nicotinic acid methylester (0.5g, 2.14 mmol) in DMF (1.5 mL) was added to the reaction mixture was stirred at RT overnight. The reaction mixture was quenched with water, extracted with EtOAc, the organic layer washed with water, brine, dried over Na2SO4 and volatiles removed. The residue was purified by column chromatography using 0-50% EtOAc/Hexanes to provide compound Villa (260 mg).

Reference： [1]Patent: WO2009/140553,2009,A2 .Location in patent: Page/Page column 71

39
[ 1953-54-4 ]
[ 7580-85-0 ]
[ 604009-32-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	Stage #1: tert-butyl glycidyl ether With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 0℃; for 0.333333h; Stage #2: indol-5-ol In dichloromethane at 0℃; for 5h;	88 Synthetic Transformation of Intermediates:; O-Alkylations :; PREPARATION 88; 5- (2- (tert-butoxy) ethoxy)-lH-indole; Add triphenylphosphine (600 mg, 2.29 mmol) to a solution of diethyl azodicarboxylate (0. 36 mL, 2.29 mmol) in methylene chloride (10 mL) at 0°C followed by ethylene glycol mono-t-butyl ether (0.30 mL, 2.29 mmol), and stir the mixture for 20 minutes at 0°C. Add 5-hydroxyindole (200 mg, 1.5 mmol), remove the cold bath, and stir for 5 hours. Add water (2 mL), transfer the resultant mixture to a separatory funnel, and separate the layers. Wash the organic layer with 0.1 N aqueous HCl and brine, then dry over sodium sulfate, filter, and concentrate. Purification by flash chromatography and eluting with hexane: ethyl acetate gives 127 mg (36%) of the title compound as a light yellow solid. Mass spectrum: electrospray (m/z) 232 (M--1).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2003/76398, 2003, A2 Location in patent: Page/Page column 35-36

40
[ 570407-87-3 ]
[ 7580-85-0 ]
[ 570408-11-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl glycidyl ether With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.666667h; Stage #2: 3,4,5-trifluorobenzoic acid 2-tert-butoxyethyl ester In tetrahydrofuran at -78 - 20℃; for 1.5h;	98 Reference Example 98 To a solution of 1.52 g of 3,4,5-trifluorobenzoic acid in 15 ml of dichloromethane, 0.92 ml of oxalyl chloride was added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes and at room temperature for 80 minutes. After DMF was added dropwise, the mixture was stirred at room temperature for 1 hour. To the residue obtained by the evaporation of the solvent under reduced pressure, 20 ml of pyridine, 3.40 ml of 2-tert-butoxyethanol, and 1 fold by spatula of DMAP were added 'under ice cooling, and the mixture was stirred at room temperature overnight. After the evaporation of the solvent under reduced pressure, the residue was mixed with saturated NaHCO3 aq. extracted with EtOAc, washed with water and brine, and dried over MgSO4. The solvent was evaporated under reduced pressure to obtain 2.10 g of crude 3,4,5-trifluorobenzoic acid 2-tert-butoxyethyl ester. To a solution of 1.03 g of potassium tert-butoxide in 15 ml of THF, 1.50 ml of 2-tert-butoxyethanol was added, and the mixture was stirred for 40 minutes. The reaction solution was cooled to -78 °C, a solution of 2.10 g of crude 3,4,5-trifluorobenzoic acid 2-tert-butoxyethylester in 5 ml of THF was added thereto, and the mixture was stirred under ice cooling for 1 hour and at room temperature for 30 minutes. The reaction solution was mixed with saturated aqueous ammonium chloride, extracted with EtOAc, and washed with water and brine, and then dried over MgSO4. The residue obtained by the evaporation of the solvent under reduced pressure was purified by silica gel column chromatography (eluent: hexane-EtOAc = 100:1∼20:1) to obtain 2.24 g of 4-(2-tert-butoxyethoxy)-3,5-difluorobenzoic acid 2-tert-butoxyethyl ester.

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - EP1466912, 2004, A1 Location in patent: Page 22

41
[ 524-38-9 ]
[ 7580-85-0 ]
[ 870243-67-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl glycidyl ether In tetrahydrofuran at 0 - 5℃; for 0.25h; Stage #2: N-hydroxyphthalimide In tetrahydrofuran at 0 - 20℃;	EEE.118 A solution of 2-tert-Butoxy-ethanol (1.18 g, 10.0 mmol) and Tiphenylphosphine (2.62 g, 10.0 mmol) in THF (25 ml) was cooled to 0 °C under N2 and Diisopropyl azodicarboxylate (1.97 ml, 10.0 mmol) was added dropwise while maintaining reavtion temperature below 5 °C . The reaction was stirred an additional 15 min at 0°C and then a solution of 2-Hydroxy- isoindole-1,3-dione (1.63 g, 10.0 mmol) in THF (40 ml) was added dropwise over about 20 min. The reaction was allowed to come slowly to room temperature with stirring overnight. Solvents were removed under reduced pressure and the mixture was purified by silica gel chromatography using 7 : 3 Heptane : EtOAc as eluant. Product fractions were combined and concentrated to 1.48 g (5.63 mmol) of an oil which crystallized on standing. ¹H NMR (d6- DMSO, 400 MHz) : (at) 7.86 (4H, s), 4.24-4.28 (2H, m), 3.60-3.64 (2H, m), 0.99 (9H, s) ; RP- HPLC (Table 1, Method m) Rt = 3.45 min.

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - WO2005/110410, 2005, A2 Location in patent: Page/Page column 292-293

42
[ 7580-85-0 ]
C₁₁H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2.1: diethyl ether / 0 °C 3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 4.1: sodium hydride / tetrahydrofuran / 0 °C 4.2: 20 °C

Reference： [1]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]

43
[ 7580-85-0 ]
C₁₁H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2.1: diethyl ether / 0 °C 3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 4.1: sodium hydride / tetrahydrofuran / 0 °C 4.2: 20 °C 5.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C

Reference： [1]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]

44
[ 7580-85-0 ]
[ 1392278-12-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2.1: diethyl ether / 0 °C 3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 4.1: sodium hydride / tetrahydrofuran / 0 °C 4.2: 20 °C 5.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C 6.1: tetrahydrofuran; diethyl ether / 0 °C 7.1: [2,2]bipyridinyl; silver hexafluoroantimonate; palladium dichloride / methanol; water / 60 °C / Inert atmosphere

Reference： [1]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]

45
[ 7580-85-0 ]
[ 1392278-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2.1: diethyl ether / 0 °C 3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 4.1: sodium hydride / tetrahydrofuran / 0 °C 4.2: 20 °C 5.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C 6.1: tetrahydrofuran; diethyl ether / 0 °C

Reference： [1]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]

46
[ 7580-85-0 ]
[ 57018-52-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2: diethyl ether / 0 °C

Reference： [1]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]

47
[ 7580-85-0 ]
[ 28047-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2: diethyl ether / 0 °C 3: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve

Reference： [1]Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. [Chemistry - A European Journal, 2012, vol. 18, # 22, p. 6907 - 6914]

48
[ 578-67-6 ]
[ 7580-85-0 ]
C₁₅H₁₉NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 20℃;	Quinolin-5-ol (100 mg, 0.689 mmole) and PPh3 (235 mg, 0.896 mmole) were taken up in toluene (3 mL). To this was added 2-tert-butoxyethanol (0.118 mL, 0.896 mmole) then DIAD (0.174 mL, 0.896 mmole) at RT. After stirring overnight the mixture was concentrated. Flash column chromatography (Biotage-SNAP-lOg Si02, 0-50percent EtOAc hexanes) gave a clear oil which was sufficiently pure for use in the next step. The impure material from above was taken up in 3 mL TFA. After 4 hr the mixture was concentrated. The residue was taken up in MeOH then passed through Dowex 1x2-400 ion exchange resin (prewashed with 1M NaOH, H20, MeOH) washing with MeOH. The filtrate was concentrated. Flash column chromatography (Biotage-SNAP-lOg Si02, 0-100percentEtOAc/hexanes) gave the title compound (108 mg, 83percent) as a white solid. 1H NMR (400 MHz, CDCI3): 8 8.92 (dd, J = 4.2, 1.7 Hz, 1 H); 8.60 (dd, J = 8.5, 1.6 Hz, 1 H); 7.73 (d, J = 8.6 Hz, 1 H); 7.61 (t, J = 8.1 Hz, 1 H); 7.39 (dd, J = 8.5, 4.2 Hz, 1 H); 6.90 (d, J = 7.7 Hz, 1 H); 4.30 (t, J = 4.5 Hz, 2 H); 4.13 (bs, 2 H); 2.07 (s, 1 H).

Reference： [1]Patent: WO2013/9582,2013,A1 .Location in patent: Page/Page column 33; 34

49
[ 7580-85-0 ]
4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt [ No CAS ]
N-[6-[2-(1,1-dimethylethoxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.8%	With sodium hydroxide In toluene at 55℃;
	With sodium hydroxide

Reference： [1]Harrington, Peter J.; Khatri, Hiralal N.; DeHoff, Brad S.; Guinn, Martin R.; Boehler, Mark A.; Glaser, Karl A. [Organic Process Research and Development, 2002, vol. 6, # 2, p. 120 - 124]
[2]Raju, K. Rajasekhara; Reddy, B. Shankar; Somannavar; Sinha; Babu, P. N. Kishore; Raju, K. Mohana [Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491]

50
[ 7580-85-0 ]
[ 1595292-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / -41 °C 2: iron; ammonium chloride / ethanol 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

Reference： [1]Olberg, Dag Erlend; Andressen, Kjetil Wessel; Levy, Finn Olav; Klaveness, Jo; Haraldsen, Ira; Sutcliffe, Julie L. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1846 - 1850]

51
[ 7580-85-0 ]
[ 918444-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / -41 °C 2: iron; ammonium chloride / ethanol

Reference： [1]Olberg, Dag Erlend; Andressen, Kjetil Wessel; Levy, Finn Olav; Klaveness, Jo; Haraldsen, Ira; Sutcliffe, Julie L. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1846 - 1850]

52
[ 7580-85-0 ]
4-(2-(tert-butoxy)ethoxy)-2,6-dimethoxyaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; palladium diacetate; 5-di(1-adamantylphosphino)-1-(1,3,5-triphenyl-1H-pyrazol-4-yl)-1H-pyrazole / 80 °C / Inert atmosphere; Schlenk technique 2: iron; ammonium chloride / ethanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: OSLO UNIVERSITY HOSPITAL HF; UNIVERSITY OF OSLO - WO2014/184682, 2014, A1

53
[ 7580-85-0 ]
[ 815632-47-4 ]
5-(2-(tert-butoxy)ethoxy)-1,3-dimethoxy-2-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 5-di(1-adamantylphosphino)-1-(1,3,5-triphenyl-1H-pyrazol-4-yl)-1H-pyrazole; palladium diacetate; caesium carbonate at 80℃; Inert atmosphere; Schlenk technique;	5-(2-(tert-butoxy)ethoxy)-1,3-dimethoxy-2-nitrobenzene To a stirred solution of CS2CO3 (391 mg, 1.2 mmol), 5-di(l-adamantylphosphino)-l-(l,3,5-triphenyl-lH-pyrazol-4-yl)-lH- pyrazole (ll mg, 0.017 mmol), and palladium(ll) acetate (l. 8 mg, 1 mol %) in 2 mL dry toluene under argon in a 25 mL Schlenk tube at 80°C, DMB-01 (200 mg, 0.8 mmol) and 2-tert-butoxyethanol (284 mg, 2.4 mmol) were added. The sealed reaction mixture was stirred at 80°C overnight. After cooling, the reaction mixture was diluted with 10 ml ethyl acetate and filtered through celite and concentrated. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) affording DMB-07 as an oil (156 mg, 68%). NMR (600 MHz, CDCI3): δ 6.17 (s, 2H), 8 4.11 (t, J= 5.3, 2H), 8 3.84 (s, 6H), δ 3.72 (t, J= 5.3, 2H), δ 1.24 (s, 9H); 13C NMR (151 MHz, CDCI3) 8 161.78, 153.39, 91.68, 73.71, 70.06, 68.80, 60.43, 56.54, 27.63; HRESIMS [M + H]+ m/z 300.1442 (calculated for C14H21NO6, 300.1442).

Reference： [1]Current Patent Assignee: OSLO UNIVERSITY HOSPITAL HF; UNIVERSITY OF OSLO - WO2014/184682, 2014, A1 Location in patent: Page/Page column 28

54
[ 7580-85-0 ]
[ 1393813-42-7 ]
[ 1393813-43-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: N-5-(4-bromophenyl)-6-chloro-4-pyrimidinyl-N‘-propylsulfamide With potassium <i>tert</i>-butylate In toluene at 20℃; for 0.0833333h; Stage #2: tert-butyl glycidyl ether In toluene at 85℃; for 2h; Stage #3: With titanium tetrachloride In toluene at 35℃; for 20h;	3 Example 3: N-(5-(4-bromophenyl)-6-(2-hydroxyethoxy)pyrimidin-4-yl)propane- 1-sulfamide (one pot preparation): Example 3: N-(5-(4-bromophenyl)-6-(2-hydroxyethoxy)pyrimidin-4-yl)propane- 1-sulfamide (one pot preparation):N-(5-(4-bromophenyl)-6-chloropyrimidin-4-yl)propane-1-sulfamide (100 g; 0.246 mol; see Preparation A) and KOtBu (110 g; 0.99 mol; 4.0 eq.) were charged into a 2 L reactor. Toluene (1 L) was added. The resulting suspension was stirred at 20°C for 5 mm. 2-(tert-butoxy)ethanol (97 mL; 0.74 mol; 3.0 eq.) was added dropwise. After completion of the addition, the reaction mixture was heated to 85°C for 2 h. After completion of the reaction, the mixture was cooled down to 20°C. Water (0.5 L) was added, followed by the addition of 10% aq. citric acid (0.5 L). The layers were separated. The org. phase was washed with brine 3 times (0.5 L each) and azeotropically dried with toluene (1 L) to a volume of approx. 1 L. The reaction mixture was heated to 50°C. A 1M solution of TiC14 in toluene (420 mL, 0.42 mol; 1.7 eq.) was added dropwise with vigorous stirring. After completion of the addition, it was stirred at 35°C for 20 h. Water (0.75 L) was added and the resulting beige suspension was stirred for 15 h. It was filtered off, rinsed with toluene (300 mL) and dried to afford the title compound as a white solid (91 g; 86% yield; purity (LC-MS): 100% a/a).The product had NIVIR data equivalent to those reported in Bolli et al., J. Med. Chem. (2012), 55, 7849-7861.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2014/155304, 2014, A1 Location in patent: Page/Page column 27; 28

55
[ 7580-85-0 ]
[ 1393813-42-7 ]
N-(5-(4-bromophenyl)-6-(2-(tert-butoxy)ethoxy)pyrimidin-4-yl)propane-1-sulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-5-(4-bromophenyl)-6-chloro-4-pyrimidinyl-N‘-propylsulfamide With potassium <i>tert</i>-butylate In toluene at 20℃; for 0.0833333h; Stage #2: tert-butyl glycidyl ether In toluene at 85℃; for 2h;	1 Example 1: N-(5-(4-bromophenyl)-6-(2-(tert-butoxy)ethoxy)pyrimidin-4-yl)propane- 1-sulfamide: Variant 3:N-(5 -(4-bromophenyl)-6-chloropyrimidin-4-yl)propane- 1 -sulfamide (35 g, 86 mmol; see Preparation A) and KOtBu (38.7 g, 0.35 mol, 4.0 eq.) were charged into a round-bottom flask. Toluene (350 mL) was added. The resulting suspension was stirred at 20°C for 5 mi 2-(tert-butoxy)ethanol (34.0 mL, 0.26 mol, 3.0 eq.) was added dropwise. After completion of the addition, the reaction mixture was heated to 85°C for 2 h. The mixture was cooled down to 20°C. Water (0.5 L) was added, followed by the addition of 10% aq. citric acid (0.5 L). The layers were separated. The org. phase was washed with brine 3 times (0.5 L each) and concentrated to dryness to afford the crude expected product as a brown oil (37.8 g, 90% yield).The product had NIVIR data equivalent to those obtained for the product of Variant 1.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2014/155304, 2014, A1 Location in patent: Page/Page column 26

56
[ 7580-85-0 ]
[(3aR,7aR)-7a-(3-fluoro-2-pyridyl)-3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-yl]-(3-chloro-4-fluoro-phenyl)methanone [ No CAS ]
[(3aR,7aR)-7a-[3-(2-tert-butoxyethoxy)-2-pyridyl]-3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-yl]-[4-(2-tert-butoxyethoxy)-3-chloro-phenyl]methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: tert-butyl glycidyl ether With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.416667h; Stage #2: [(3aR,7aR)-7a-(3-fluoro-2-pyridyl)-3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-yl]-(3-chloro-4-fluoro-phenyl)methanone In N,N-dimethyl-formamide; mineral oil at 80℃; for 1h;	2 Step 2: [(3aR,7aR)-7a- [3-(2-tert-butoxyethoxy)-2-pyridylj - 3a,4,6,7-tetrahydro- [1,31 dioxolo [4,5-cl pyridin-5-ylj - [4-(2-tert-butoxyethoxy)-3- chioro-phenyll methanone [00341J Step 2: [(3aR,7aR)-7a- [3-(2-tert-butoxyethoxy)-2-pyridylj - 3a,4,6,7-tetrahydro- [1,31 dioxolo [4,5-cl pyridin-5-ylj - [4-(2-tert-butoxyethoxy)-3- chioro-phenyll methanone [00342j In a vial, 2-tert-butoxyethanol (155 mg, 1.31 mmol) was dissolved in DMF (500 jiL). NaH (53 mg, 1.3 mmol) (60% oil dispersion) was added in small portions and the suspension was stirred at rt for 25 mi [(3aR,7aR)-7a-(3-fluoro-2-pyridyl)-3 a,4,6,7-tetrahydro- [1,3] dioxolo [4,5 -c]pyridin-5 -yl] -(3 -chloro-4- fluoro-phenyl)methanone (50 mg, 0.13 mmol) as a solution in DMF (100 jiL) was added and the reaction mixture was stirred at 80 °C for 1 h. The reaction mixture was quenched by the addition of water. The resultant mixture was extracted with DCM(3x). The combined extracts were dried over sodium sulfate and the volatiles were removed under reduced pressure. The crude product was purified by reverse phase HPLC (HC1 as a modifier) providing [(3aR,7aR)-7a-[3-(2-tert-butoxyethoxy)-2- pyridyl] -3 a,4,6,7-tetrahydro-[ 1,3] dioxolo [4,5 -c]pyridin-5 -yl]- [4-(2-tert-butoxyethoxy)- 3-chloro-phenyl]methanone (38 mg, 47 %) as a colorless solid. ESI-MS mlz calc.576.3, found 577.0 (M+1) Retention time: 1.48 min(3 minrun).

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2015/6280, 2015, A1 Location in patent: Paragraph 00338; 00341; 00342

57
[ 7580-85-0 ]
[ 403-01-0 ]
C₁₄H₁₉FO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With di-isopropyl azodicarboxylate; In tetrahydrofuran; at 20℃; for 1h;	[1428] Diisopropylazadicarboxylate (0.29 mL, 1 .5 mmol) was added to a solution of <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong> (0.21 g, 1.2 mmol, ethyl glycol mono-to -butyl ether (0.32 mL, 2.5 mmol) and polymer bound triphenylphosphine ( 1.1 g, 1.9 mmol) in THT (5 mL). The mixture was stirred at r.t. for 1 h. The resin was removed by filtration, and the mixture was concentrated. The product was purified by column chromatography (hexane:EA) to 476-1 (0.34 g, 98percent).

Reference： [1]Patent: WO2015/26792,2015,A1 .Location in patent: Paragraph 1428

58
[ 7580-85-0 ]
[ 403-01-0 ]
C₁₃H₁₇FO₄ [ No CAS ]

Reference： [1]Patent: WO2015/26792,2015,A1

59
[ 7580-85-0 ]
C₃₈H₄₃N₃O₄ [ No CAS ]
C₄₁H₅₂N₃O₅⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.24 g	Stage #1: tert-butyl glycidyl ether With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at -75℃; for 0.333333h; Inert atmosphere; Stage #2: C₃₈H₄₃N₃O₄ In dichloromethane at -75 - 20℃; Inert atmosphere; Stage #3: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane In dichloromethane Inert atmosphere;

Reference： [1]Qian, Wen-Jian; Burke, Terrence R. [Organic and Biomolecular Chemistry, 2015, vol. 13, # 14, p. 4221 - 4225]

60
[ 2075-46-9 ]
[ 7580-85-0 ]
1-(2-(tert-butoxy)ethyl)-4-nitro-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;	34A 34A. Preparation of l-(2-(tert-butoxy)ethyl)-4-nitro-lH-pyrazole DIAD (8.60 rnL, 44.2 mmol) was added to a solution of 4-nitro- lH-pyrazole (5 g, 44.2 mmol), 2-(tert-butoxy)ethanol (5.23 g, 44.2 mmol), and PPh3 (11.60 g, 44.2 mmol) in THF (40 mL) and stirred at rt for 2 h. The reaction mixture was then quenched with water and purified using silica gel chromatography to yield 1 -(2-(tert-butoxy)ethyl)-4- nitro-lH-pyrazole (10.45 g, 44.1 mmol, 95% yield). NMR (400MHz, CDC13) δ 8.24 (s, 1H), 8.05 (s, 1H), 4.26 (t, J=5.1 Hz, 2H), 3.76 - 3.63 (m, 2H), 1.10 (s, 9H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/116882, 2015, A1 Location in patent: Page/Page column 137

61
[ 68500-37-8 ]
[ 7580-85-0 ]
C₁₆H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 2-(tert-butoxy)ethanol (708mg, 6mmol) in DMF (40mL) was added with NaH (480mg, 12mmol). After stirred for 15min, 7-substitued-4-chloroquinoline (4mmol) was added to the mixture and then stirred at 40°C for overnight. The reaction mixture was quenched with water and extracted with ethyl acetate (30mL×3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 9

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 191 - 200
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 830 - 834

62
[ 75090-52-7 ]
[ 7580-85-0 ]
C₁₅H₁₈BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 2-(tert-butoxy)ethanol (708mg, 6mmol) in DMF (40mL) was added with NaH (480mg, 12mmol). After stirred for 15min, 7-substitued-4-chloroquinoline (4mmol) was added to the mixture and then stirred at 40C for overnight. The reaction mixture was quenched with water and extracted with ethyl acetate (30mL×3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 9

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 115,p. 191 - 200
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 830 - 834

63
[ 7580-85-0 ]
C₂₀H₂₃N₅O [ No CAS ]
C₂₆H₃₅N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃;

Reference： [1]Stauffer, Frédéric; Cowan-Jacob, Sandra W.; Scheufler, Clemens; Furet, Pascal [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 2065 - 2067]

64
[ 7580-85-0 ]
C₅₀H₈₀N₈O₁₃PPol [ No CAS ]
C₄₈H₇₈N₈O₁₄P⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl glycidyl ether; C₅₀H₈₀N₈O₁₃PPol With triphenylphosphine; diethylazodicarboxylate Stage #2: With triisobutylsilane; trifluoroacetic acid In water for 4h;	I.2.5.8 General procedure: C) Peptide Cleavage and Purification (0447) Peptide resins (200 mg) were cleaved by treatment with trifluoroacetic acid:triisbutylsilane:H2O (90:5:5) (5 mL, 4 h). The resin was removed by filtrations and the filtrate was concentrated under vacuum, then peptide was precipitated by the addition of precipitated with diethyl ether and the precipitate washed with ether. The resulting solid was dissolved in 50% aqueous acetonitrile (5 mL) and purified by reverse phase preparative HPLC using a Phenomenex C18 column (21 mm dia×250 mm, cat. no: 00G-4436-P0) with a linear gradient from 0% aqueous acetonitrile (0.1% trifluoroacetic acid) to 100% acetonitrile (0.1% trifluoroacetic acid) over 30 minutes at a flow rate of 10.0 mL/minute. Lyophilization gave the products as white powders.

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - US2016/39872, 2016, A1 Location in patent: Paragraph 0447; 0468; 0472

65
[ 7580-85-0 ]
[ 1023742-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / tert-butyl methyl ether / 2 h / 0 - 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 80 °C 3: ammonia / ethanol / 912.06 Torr
	Multi-step reaction with 2 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.25 h / 0 - 5 °C 1.2: 0 - 20 °C 2.1: methylhydrazine / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: BEIJING LAVIANA PHARMATECH - CN103304356, 2016, B
[2]Current Patent Assignee: ABBOTT LABORATORIES INC - WO2005/110410, 2005, A2

66
[ 7580-85-0 ]
methyl 3-iodo-1-[(4-methoxyphenyl)methyl]-1H-thieno[3,2-c]pyrazole-5-carboxylate [ No CAS ]
3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-thieno[3,2-c]pyrazole-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate In toluene at 100℃; Inert atmosphere;	46.1 Step a: 3-Iodo-1- (4-methoxybenzyl) lH-thieno [3,2-c] pyrazole-5-carboxylate (1.29g, 3mmol) (see preparation step synthesis Example 34), 3,4,7,8- tetramethyl-1,10-phenanthroline (472mg, 2mmol), cesium carbonate (4.89g, 15mmol), ethylene glycol mono-t-butyl ether (106mg, 0.9 mmol), cuprous iodide (0.29 g, 1.5mmol) were mixed in a single-neck flask, toluene (5mL), under nitrogen, 100 ° C and stirred overnight.Cooled to room temperature, water was added to the system, the ethyl acetate extracts were combined, dried over anhydrous sodium sulfate, and concentrated to give 3- (2-tert-butoxy ethoxy) -1- (4-methoxybenzyl ) lH-thieno [3,2-c] pyrazole-5-carboxylic acid The crude, yellow-green solid 3.4g

Reference： [1]Current Patent Assignee: SHANGHAI HUILUN LIFE SCIENCE TECHNOLOGY CO LTD - CN103467481, 2016, B Location in patent: Paragraph 0600 - 0602

67
[ 185756-31-4 ]
[ 7580-85-0 ]
C₃₂H₄₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8g	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 5 - 20℃; for 4h; Inert atmosphere;	Then an agitator, condenser, and a reaction vessel equipped with a thermometer glycol mono-t- butyl ether, 4.5g (38 mmol), the compound shown in the formula (3) 6.2g (16 mmol), triphenylphosphine 9.6g (37 mmol) was charged to 200ml and THF, cooling the reactor under a nitrogen gas atmosphere to less than 5 .Then diisopropyl ah Jody acid was added dropwise to the 7g (35 mmol) slowly.After the addition was completed, it was 4 hours at room temperature.After the reaction, methanol / pure water was distilled off to cool the reaction solution was concentrated to less than 5 the THF and then added dropwise to 100ml = 300 / 60ml solution, and reprecipitated.After filtering the precipitate, and dried to synthesize the compound shown in formula (4) 8g.

Reference： [1]Current Patent Assignee: DIC CORP. - KR101523330, 2015, B1 Location in patent: Paragraph 0045; 0107; 0108

68
[ 7580-85-0 ]
methyl 7-(benzyloxy)-1H-indole-5-carboxylate [ No CAS ]
C₁₆H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triphenylphosphine at 20℃; for 2h;	110 Diisopropylazodicarboxylate (53 μL, 0.27 mmol) was added drop wise to a solution of 109-1 (47 mg, 0.25 mmol), 2-(tert-butoxy)ethanol (44 mg, 0.27 mmol) and triphenylphosphine (71 mg, 0.27 mmol). The reaction was stirred at RT for 2 h. The reaction was concentrated and the product 124-2 (50 mg, 68%) purified by flash chromatography (hexane/ethyl acetate). 1H NMR (400 MHz, CDCl3): δ 9.31 (br. s, 1H), 8.08 (s, 1H), 7.37 (s, 1H), 7.19-7.20 (m, 1H), 6.58-6.59 (m, 1H), 5.28 (t, J=5.2, 2H), 3.89 (s, 3H), 3.77 (t, J=5.2, 2H), 1.26 (s, 9H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2016/244460, 2016, A1 Location in patent: Paragraph 0704; 0706

69
[ 15231-91-1 ]
[ 7580-85-0 ]
C₁₆H₁₉BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18 g	With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 5 - 20℃; for 5h;	1 (Embodiment 1) The stirring device, a cooler, a reaction vessel and 6-bromo-2-naphthol 20g (90 millimols), (107 millimols) ethylene glycol mono tar plain gauze leave chill ether 12g, triphenylphosgene 35g (134 millimols), a ketone dichlomethane 300 ml, reaction vessel is cooled to 5 °C. Thereafter, dicaprylate diazoacetic carboxylic acid (DIAD) 22g (107 millimols) is dropped. After dropping, 5 and the reaction is terminated by stirring at room temperature. After completion of the reaction, adding dichlomethane 200 ml, pure water, saturated saline solution is washed with organic layer. After distilling, refining is represented by (1) by using the glycopeptide compd. 18g is obtained.
18 g	With triphenylphosphine In dichloromethane at 5 - 20℃; for 5h;	1 20 g (90 mmol) of 6-bromo-2-naphthol, 12 g (107 mmol) of ethylene glycol monotericyl butyl ether, 35 g (134 mmol) of triphenylphosphine, 6 g of dichloromethane And the reaction vessel was cooled to 5 ° C. Thereafter, 22 g (107 mmol) of diisopropyl diazocarboxylate (DIAD) was added dropwise.After completion of the dropwise addition, the reaction was terminated by stirring at room temperature for 5 hours. After completion of the reaction, 200 ml of dichloromethane was added, and the organic layer was washed with pure water and saturated brine. After distilling off the solvent, purification by silica gel column gave 18 g of the compound represented by (1).

Reference： [1]Current Patent Assignee: DIC CORP. - JP2016/169218, 2016, A Location in patent: Paragraph 0078-0079
[2]Current Patent Assignee: DIC CORP. - JP6031781, 2016, B2 Location in patent: Paragraph 0078; 0079

70
[ 7580-85-0 ]
C₂₂H₂₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 5 h / 5 - 20 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 5 h / 70 °C
	Multi-step reaction with 2 steps 1: triphenylphosphine / dichloromethane / 5 h / 5 - 20 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 5 h / 70 °C

Reference： [1]Current Patent Assignee: DIC CORP. - JP2016/169218, 2016, A
[2]Current Patent Assignee: DIC CORP. - JP6031781, 2016, B2

71
[ 7580-85-0 ]
C₂₆H₂₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 5 h / 5 - 20 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 5 h / 70 °C 3: dmap; diisopropyl-carbodiimide / dichloromethane / 5 h / 5 - 20 °C / Cooling with ice; Inert atmosphere
	Multi-step reaction with 3 steps 1: triphenylphosphine / dichloromethane / 5 h / 5 - 20 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 5 h / 70 °C 3: dmap; diisopropyl-carbodiimide / dichloromethane / 5 h / 5 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DIC CORP. - JP2016/169218, 2016, A
[2]Current Patent Assignee: DIC CORP. - JP6031781, 2016, B2

72
[ 107-21-1 ]
[ 75-65-0 ]
[ 7580-85-0 ]

Yield	Reaction Conditions	Operation in experiment
10.1%Chromat.	With activated clay In 1,2-dimethoxyethane at 80℃; for 6h;	25 The same apparatus as in Example. 13, tert-butanol 5 g (67 mmol), ethylene glycol 4.2 g (67 mmol), dimethoxyethane 25 g, activated clay 1g placed and stirred for 6 hours at 80 ° C.. The reaction mixture was analyzed by gas chromatography, 66.6% tert-butanol, 21.8 percent ethylene glycol, 10.1% ethylene glycol monobutyl -tert- butyl ether was detected. Diethylene glycol and di -tert- butyl ether was not detected at all.

Reference： [1]Current Patent Assignee: YUKI GOSEI KOGYO CO., LTD. - JP2016/160224, 2016, A Location in patent: Paragraph 0042

73
[ 7580-85-0 ]
[ 358-23-6 ]
2-tert-butoxyethyl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine; triethylamine; N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 0℃; for 1h;	3.1A 2-tert-Butoxyethyl trifluoromethanesulphonate At -78°C, 473 mg (4.00 mmol) of 2-tert-butoxyethanol and 0.75 ml (4.40 mmol, 1.1 eq.) of trifluoromethanesulphonic anhydride in the presence of 0.61 ml (4.4 mmol, 1.1 eq.) oftriethylamine were reacted according to General Method 7A. The crude product was reacted in the next step without further purification. ‘H-NMR (400 MHz, DMSO-d6): ö [ppm] = 4.38 (t, 2H), 3.57 (t, 2H), 1.19 (s, 9H). A solution of the appropriate alcohol (1 eq.) was initially charged in dichloromethane (0.1-1 M), and at -78°C to 0°C lutidine (1.1-1.5 eq.) or triethylamine (1.1-1.5 eq.) or iN35 diisopropylethylamine (1.1-1.5 eq.) and trifluoromethanesulphonic anhydride (1.05-1.5 eq.) were added in succession. The reaction mixture was stirred at -78°C to 0°C for another 1 h and then diluted with triple the amount (based on the reaction volume) of methyl tert-butyl ether. The organic phase was washed three times with a 3:1 mixture of saturated aqueous sodium chloride solution/iN hydrochloric acid and finally with saturated aqueous sodium bicarbonate solution,5 dried (sodium sulphate or magnesium sulphate) and filtered, and the solvent was removed under reduced pressure. The crude product was used in the next step without further purification.
	With 2,6-dimethylpyridine In dichloromethane at 30℃; for 2h; Cooling with ice;	108.1; 109.1 2-(tert-butoxy)ethyl trifluoromethanesulfonate 108b Step 1 2-(tert-butoxy)ethyl trifluoromethanesulfonate 108b 2-tert-butoxyethanol 108a (300 mg, 2.54 mmol) was dissolved in 8 mL of dichloromethane, then 2,6-dimethylpyridine (299.22 mg, 2.79 mmol) was added in an ice bath, and trifluoromethanesulfonic anhydride (787.87 mg, 2.79 mmol) was added dropwise. After completion of the addition, the reaction solution was stirred for 1 hour in an ice bath, naturally warmed up to room temperature and stirred for 1 hour. The reaction solution was added with 30 mL of dichloromethane, and washed with 20 mL of water. The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound 108b (550 mg), which was directly used in the next reaction without purification.
	Stage #1: tert-butyl glycidyl ether With 2,6-dimethylpyridine In dichloromethane Cooling with ice; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 20℃; Cooling with ice;	First Step 2-(Tert-butoxy)ethyl trifluoromethanesulfonate 1b [0098] 2-Tert-butoxy ethanol 1a (300 mg, 2.54 mmol) is dissolved in 8 mL of No. dichloromethane, added with No. 2,6-dimethylpyridine (299.22 mg, 2.79 mmol) in an ice bath, and added dropwise with No. trifluoromethanesulfonic anhydride (787.87 mg, 2.79 mmol); after completion of the dropwise addition, the reaction was stirred for 1 hour in an ice bath, allowed to naturally warm to room temperature and then stirred for 1 hour. The reaction solution was added with 30 mL of dichloromethane and washed with 20 mL of No. water; the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain crude No.1 title compound 1b (550 mg); the product was used directly for the next reaction without purification.

With pyridine In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;

122.1 first step 2-(tert-Butoxy)ethyl trifluoromethanesulfonate Ethylene glycol mono-tert-butyl ether 122a (2 g, 16.92 mmol) was dissolved in dichloromethane (20 mL),Pyridine (1.61 g, 20.31 mmol) was added,Cooled to 0°C under nitrogen atmosphere,Then, trifluoromethanesulfonic anhydride (5.25 g, 18.62 mmol) was slowly added dropwise, and stirring was continued for 20 minutes under an ice bath.Dichloromethane (100 mL) was added to the reaction solution to dilute, washed with 2M dilute hydrochloric acid (50 mL×2) and saturated sodium chloride solution (50 mL) successively,The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.The crude product 2-(tert-butoxy)ethyl trifluoromethanesulfonate 122b (4.24 g) was obtained, which was directly used in the next reaction.

Reference： [1]Current Patent Assignee: BAYER AG; MUELLERSTRASSE 178 BERLIN 13353 GERMANY - WO2017/5725, 2017, A1 Location in patent: Page/Page column 62-63; 102-103
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3486242, 2019, A1 Location in patent: Paragraph 0384-0385
[3]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - US2021/122714, 2021, A1 Location in patent: Paragraph 0097-0098
[4]Current Patent Assignee: HISUN ACCURAY THERAPEUTICS; HISUN GROUP CO., LTD. - WO2022/57849, 2022, A1 Location in patent: Page/Page column 159-160

74
[ 7580-85-0 ]
[ 4489-34-3 ]
2-(2-(tert-butoxy)ethoxy)-4,6-dichloropyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		Under nitrogen, sodium hydride (1 eq)And 2- (tert-butoxy) ethanol (1 eq)Is added to the anhydride THF and stirred for 1 hour in an ice bath.Under ice-cooling. Then, 4,6-dichloro-2-methanesulfonyl-pyrimidine (1.5 eq) is dissolved in THF and stirred overnight.After completion of the reaction, the solvent was dried with a rotary evaporator, and the EA layer was separated from the separatory funnel by using NaHCO 3 solution / EA and dried by drying with MgSO 4.Filter solution was removed by rotary evaporator and column. Yield: white oil 91%.

Reference： [1]Patent: KR2017/41562,2017,A .Location in patent: Paragraph 0392-0393

75
[ 178984-69-5 ]
[ 7580-85-0 ]
C₁₇H₂₁NO₄ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 830 - 834

76
[ 7580-85-0 ]
methyl 5-(thiazol-2-yl)-2H-1,2,6-thiadiazine-3-carboxylate 1,1-dioxide [ No CAS ]
methyl 2-(2-(tert-butoxy)ethyl)-5-(thiazol-2-yl)-2H-1,2,6-thiadiazine-3-carboxylate 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 60℃; for 16h; Inert atmosphere;	Method B (Alkylation using Mitsunobu reaction) General procedure: To a stirred solution of cyclic sulphonamide (1 eq.) in dry THF (4V) at 0 °C under Ar atmosphere, TPP (2 eq.) and methanol (10 eq.) was added and stirred at 0 °C for 45 min. To this solution, DEAD/DIAD (2 eq.) was added slowly and resulting reaction mixture (color change to dark brown) was heated at 60 oC for 16 h. The progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture concentrated under vacuum, residue obtained was taken in diethyl ether, stirred for 30 min. and filtered. The solid obtained was further stirred in methanol for 30 min., filtered and dried in vacuo to afford N-alkylated desired compound (Note: a few compounds were further purified using silica gel column chromatography).

Reference： [1]Current Patent Assignee: ASSEMBLY BIOSCIENCES, INC. - WO2018/160878, 2018, A1 Location in patent: Page/Page column 62; 101

77
[ 112-42-5 ]
[ 7580-85-0 ]
[ 38471-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl glycidyl ether With trifluorormethanesulfonic acid; triethylamine In dichloromethane at -20℃; for 6h; Stage #2: undecyl alcohol With tetrabutylammomium bromide; caesium carbonate In tetrahydrofuran at 120℃; for 3h;	1 Embodiment 1 The reaction bottle into the 59 g 2 - tert-butoxy ethanol, 65 g triethylamine and 300 ml of dichloromethane, cooled to -20 °C, slowly dropping 156 g trifluoromethanesulfonic anhydride. The completion of the dropping, stirring for 6 hours; cold water quenching reaction, liquid, organic phase dried, concentrated.Concentrate shifts into 1 in boost strength cauldron, respectively adding 300 ml of tetrahydrofuran, is n-undecanol 95 g, 10 g tert-butylammonium bromide and 110 g cesium carbonate, after sealing with the temperature rising to 120 °C, thermal insulation reaction 3 hours; cooling to heating, suction filtering to remove the solid, concentrated to remove the solvent, adding water and dichloromethane stirring, liquid. The organic phase by adding 50 ml of trifluoroacetic acid, at room temperature the reaction is complete, adding 250 ml of water quenching reaction, liquid, aqueous phase dichloromethane is used for extraction, the combined organic phase, concentrated, distilled under reduced pressure to obtain 56 g Hendecane phenoxy ethanol, the product purity 99.6%.

Reference： [1]Current Patent Assignee: SUZHOU ZENONG BIOTECHNOLOGY - CN108558709, 2018, A Location in patent: Paragraph 0046-0049; 0051-0053; 0055-0057; 0059-0061; 0063-0

78
[ 7580-85-0 ]
C₁₃H₁₆O₃ [ No CAS ]
C₁₉H₂₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.029 g	With triphenylphosphine; diethylazodicarboxylate In dichloromethane; toluene at 0 - 20℃; Inert atmosphere;	1.7 To a solution of 7 (2.04 g, 9.26 mmol) in dichloromethane (46 mL) at 0 °C under argon, ethylene glycol mono tert-butyl ether (1.58 mL, 12.04 mmol) was added by syringe followed by triphenylphosphine (3.65 g, 13.9 mmol). The mixture was stirred 10 minutes, then a solution of diethyl azodicarboxylate (40% by weight in toluene, 6.33 mL, 13.9 mmol) was added. After stirring at room temperature overnight, TLC indicated partial conversion. Additional portions of ethylene glycol mono tert-butyl ether (0.79 mL, 6.0 mmol), triphenylphosphine (1.82 g, 7.0 mmol), and diethyl azodicarboxylate (3.2 mL, 7.0 mmol) were added, and the mixture was stirred an additional 24 hours, then was concentrated under reduced pressure. The residue was taken up in 3 : 1 hexanes:ethyl acetate and the solution was washed with water (twice) and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in 9: 1 hexanes:dichloromethane with heating to give a clear solution, that was allowed to cool to room temperature and stand overnight. Some crystals adhered to the side of the flask which were by-products from the reaction. The solution was decanted and applied directly to a 5-inch plug of silica gel, which was sequentially eluted with 9: 1 hexanes:dichlorom ethane, 19: 1 hexanes: ethyl acetate, 9: 1 hexanes: ethyl acetate and finally 3 : 1 hexanes: ethyl acetate to give 8 (2.029 g) as a pale yellow oil. A small amount of unreacted starting material (0.39 g) was also isolated.

Reference： [1]Current Patent Assignee: TEXAS HEART INSTITUTE; TEXAS CHILDREN'S HOSPITAL - WO2018/201069, 2018, A1 Location in patent: Paragraph 00141; 00153

79
[ 7580-85-0 ]
[ 668-45-1 ]
C₁₃H₁₆ClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.22 g	Stage #1: tert-butyl glycidyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-6-fluorobenzonitrile In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	1.1 To a solution of ethylene glycol mono fert-butyl ether (3.44 mL, 3.096 g, 26.2 mmol) in anhydrous tetrahydrofuran (26.2 mL) at 0 °C under argon, sodium hydride (60% dispersion in mineral oil, 655 mg, 16.4 mmol) was added in several portions. The mixture was stirred at 0 °C for 30 minutes and 2-chloro-6-fluorobenzonitrile (2.028 g, 13.1 mmol) was added. The reaction mixture was allowed to slowly warm to room temperature and was stirred overnight. The mixture was diluted with a 1 : 1 mixture of hexanes: ethyl acetate, and washed with water (twice) and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by automated silica gel chromatography (Biotage, SNAP 50 KP-Sil, 0-50% ethyl acetate in hexanes) to give 1 (3.22 g) as a colorless oil.

Reference： [1]Current Patent Assignee: TEXAS HEART INSTITUTE; TEXAS CHILDREN'S HOSPITAL - WO2018/201069, 2018, A1 Location in patent: Paragraph 00141; 00142

80
[ 7580-85-0 ]
1,8-bis(benzyloxy)-9,10-anthraquinone-3-carbonyl chloride [ No CAS ]
1,8-bis(benzyloxy)-9,10-anthraquinone-O-(2-(tert-butoxy)ethyl)-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;

Reference： [1]Tian, Wei; Li, Junying; Su, Zhengying; Lan, Fu; Li, Zhaoquan; Liang, Dandan; Wang, Chunmiao; Li, Danrong; Hou, Huaxin [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 5, p. 732 - 736]

81
[ 24065-33-6 ]
[ 7580-85-0 ]
[ 91505-31-6 ]

Yield	Reaction Conditions	Operation in experiment
95.56%	Stage #1: 5-Chlorothiophene-2-carboxylic acid With oxalyl dichloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: tert-butyl glycidyl ether With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;	37A Intermediate 37A: 2-(tert-butoxy)ethyl 5-chlorothiophene-2-carboxylate Oxalyl chloride (5.43 g, 42.80 mmol, 3.74 mL) was added dropwise to a solution of 241 5-chlorothiophene-2-carboxylic acid (5.80 g, 35.67 mmol) in 242 dichloroethane (60.00 mL) at 0°C, then 51 DMF (100.00 µL) was added, and the reaction mixture was stirred at 20°C for 2h. The reaction solution was then concentrated to dryness. The residue was redissolved in 39 tetrahydrofuran (30 mL), then a mixed solvent of 243 2-t-butyloxyethyl alcohol (4.22 g, 35.67 mmol, 4.68 mL) and 79 triethylamine (10.83 g, 107.01 mmol, 14.83 mL) in tetrahydrofuran (50.00 mL) were added dropwise at 0°C, and the reaction mixture was stirred at 20°C for 2h. After TLC showed the reaction finished, the reaction mixture was concertrated. The residue was redissolved in 40 ethyl acetate (50 mL), washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concertrated. The residue was purified by column chromatography to give the 244 title compound (9.16 g, 95.56% yield) as colorless oil. LCMS (ESI) m/z: 263 (M+1). 1HNMR (400 MHz, CHLOROFORM-d) δ ppm 1.24 (s, 9 H), 3.56-3.71 (m, 2H), 4.29-4.43 (m, 2H), 6.95 (d, J=4.02 Hz, 1H), 7.62 (d, J=4.14 Hz, 1H).

Reference： [1]Current Patent Assignee: HARBIN ZHENBAO PHARMACEUTICAL - EP3473628, 2019, A1 Location in patent: Paragraph 0229; 0230

82
[ 7580-85-0 ]
3-((3-fluoro-2-methoxyphenyl)amino)-2-(3-hydroxypyridin-4-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one [ No CAS ]
2-[3-(2-tert-butoxyethoxy)pyridin-4-yl]-3-(3-fluoro-2-methoxyanilino)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; cyanomethylenetributyl-phosphorane In toluene at 120℃; for 2.5h;	91 2-[3-(2-tert-butoxyethoxy)pyrid in-4-yl]-3-(3-fluoro-2-methoxyan ili no)-1 ,5,6,7-tetrahyd ro-4 Hpyrrolo[3,2-c]pyridin-4-one 3-(3-fluoro-2-methoxyani lino)-2-(3-hyd roxypyrid in-4-yl)-1 ,5,6 ,7-tetrahyd ro-4 H-pyrrolo[3,2-c]pyridin-4-one (Intermediate 84-1, 88.2 mg, 239 pmol) and 2-tributylphosphoranylidene)acetonitrile (82 p1, 310 pmol) were solved in 4.0 mL toluene, 2-tert-butoxyethan-1-ol (38 p1, 290 pmol) was added and the mixture was stirres 2.5 h at 12000. The reaction mixture was cooled down to rt and concentrated under reduced pressure. The residue was purified by preparative HPLCto give 38.8 mg of the yellow title compound (purity, yield).1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: 0.861 (0.75), 0.879 (1.91), 0.896 (1.01), 1.149(16.00), 1.359 (0.46), 1.374 (0.45), 2.819 (0.46), 2.836 (0.99), 2.853 (0.52), 3.403 (0.66),3.408 (0.67), 3.718 (0.56), 3.729 (0.85), 3.742 (0.64), 3.894 (4.70), 4.238 (0.60), 4.251(0.84), 4.262 (0.58), 5.982 (0.52), 6.003 (0.55), 6.596 (0.42), 6.611 (0.40), 7.125 (0.63),7.283 (0.89), 7.295 (0.90), 7.473 (1.30), 8.017 (0.92), 8.029 (0.89), 8.384 (1.51), 10.945(0.69).LC-MS (method 2): R1 = 1.10 mm; MS (ESIpos): mlz = 469 [M+H]
38.8 mg	With cyanomethylenetributyl-phosphorane In toluene at 120℃; for 2.5h;	91 Example 912-[3-(2-tert-butoxyethoxy)pyridin-4-yl]-3-(3-fluoro-2-methoxyanilino)-1 ,5,6,7-tetrahydro-4H- pyrrolo[3,2-c]pyridin-4-one 3-(3-fluoro-2-methoxyanilino)-2-(3-hydroxypyridin-4-yl)-1 ,5,6,7-tetrahydro-4H-pyrrolo[3,2- c]pyridin-4-one (Intermediate 84-1 , 88.2 g, 239 pmol) and 2- tributylphosphoranylidene)acetonitrile (82 pi, 310 pmol) were solved in 4.0 ml_ toluene, 2- tert-butoxyethan-1-ol (38 pi, 290 pmol) was added and the mixture was stirres 2.5 h at 120°C. The reaction mixture was cooled down to rt and concentrated under reduced pressure. The residue was purified by preparative HPLCto give 38.8 mg of the yellow title compound (purity, yield).1H-NMR (400 MHz, DMSO-d6) d [ppm]: 0.861 (0.75), 0.879 (1.91), 0.896 (1.01), 1.149 (16.00), 1.359 (0.46), 1.374 (0.45), 2.819 (0.46), 2.836 (0.99), 2.853 (0.52), 3.403 (0.66),3.408 (0.67), 3.718 (0.56), 3.729 (0.85), 3.742 (0.64), 3.894 (4.70), 4.238 (0.60), 4.251 (0.84), 4.262 (0.58), 5.982 (0.52), 6.003 (0.55), 6.596 (0.42), 6.61 1 (0.40), 7.125 (0.63), 7.283 (0.89), 7.295 (0.90), 7.473 (1.30), 8.017 (0.92), 8.029 (0.89), 8.384 (1.51), 10.945 (0.69).LC-MS (method 2): Rt= 1.10 min; MS (ESIpos): m/z = 469 [M+H]+

Reference： [1]Current Patent Assignee: BROAD INSTITUTE; DANA-FARBER CANCER INSTITUTE; BAYER AG - WO2019/81486, 2019, A1 Location in patent: Page/Page column 278; 279
[2]Current Patent Assignee: BROAD INSTITUTE; DANA-FARBER CANCER INSTITUTE; BAYER AG - WO2020/216774, 2020, A1 Location in patent: Page/Page column 292-293

83
[ 7580-85-0 ]
C₅₁H₇₆N₈O₁₁PPol [ No CAS ]
[ 1403265-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl glycidyl ether; C₅₁H₇₆N₈O₁₁PPol With triphenylphosphine; diethylazodicarboxylate In dichloromethane; toluene at 20℃; for 2h; Stage #2: With chlorotriisopropylsilane; trifluoroacetic acid In water at 20℃; for 4h;	1 Peptide Synthesis Procedures. General procedure: Fmoc-Thr(PO(OBzl)OH)-OH and other Fmoc protected amino acids were purchased from Novabiochem. Fmoc-His(Nπ-(CH2)8Ph)-OH was synthesized through our previous published paper [J. Org. Chem, 2011, 76, 8885.] Peptides were synthesize on NovaSyn TGR resin (Novabiochem, cat. no. 01-64-0060) using standard Fmoc solid-phase protocols in N-Methyl-2-pyrrolidone (NMP). 1-O-Benzotriazole-N,N,N',N'-tetramethyl-uronium-hexafluoro-phosphate (HBTU) (5.0 eq.), hydroxybenzotriazole (HOBT) (5.0 eq.) and N,N-Diisopropylethylamine (DIPEA) (10.0 eq.) were used as coupling reagents. The N-terminal was acetylated by 1-Acetylimidazole. Finally the resin was washed with N, N-dimethylforamide (DMF), methanol, dichloromethane and ether, and then dried under vacuum (overnight). Post-Modification of the Peptide by Mitsunobu Reaction. The above resin (200 mg, 0.04 mmol) was swelled in dichloromethane for 15 mins, treated by triphenylphosphine (262 mg, 1.0 mmol), DEAD (0.46 mL, 40% solution in toluene, 0.10 mol) and alchohol a-l (0.10 mmol) in dry dichloromethane for 2 hr at r.t., washed by dichloromethane, dried under vacuum for 2 hr before cleavage. Peptide Cleavage and Purification. Peptides were cleaved from resin (200 mg) by treatment with 5 mL of trifluoroacetic acid:triisbutylsilane:H2O (90:5:5) (4 h). The resin was filtered off and the filtrate was concentrated under vacuum, then precipitated with ether and the precipitate washed with ether. The resulting solid was dissolved in 50% aqueous acetonitrile (5 mL) and purified by reverse phase preparative HPLC using a Phenomenex C18 column (21 mm dia*250 mm, cat. no: 00G-4436-P0) with a linear gradient from 0% aqueous acetonitrile (0.1% trifluoroacetic acid) to 100% acetonitrile (0.1% trifluoroacetic acid) over 30 minutes at a flow rate of 10.0 mL/minute. Lyophilization gave the product as white powders.

Reference： [1]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - US10266565, 2019, B2 Location in patent: Page/Page column 203-208

84
[ 7580-85-0 ]
tert-butyl 4-(tert-butoxy)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxypyridine-1(2H)-yl)butyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine / dichloromethane / 2 h / 30 °C / Cooling with ice 2: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C
	Multi-step reaction with 2 steps 1.1: 2,6-dimethylpyridine / dichloromethane / Cooling with ice 1.2: 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran; water / 2 h / -78 °C

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3486242, 2019, A1
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - US2021/122714, 2021, A1

85
[ 7580-85-0 ]
4-(tert-butoxy)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxypyridine-1(2H)-yl)butyric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / dichloromethane / 2 h / 30 °C / Cooling with ice 2: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C 3: lithium hydroxide / ethanol; tetrahydrofuran / 2 h / 50 °C
	Multi-step reaction with 3 steps 1.1: 2,6-dimethylpyridine / dichloromethane / Cooling with ice 1.2: 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran; water / 2 h / -78 °C 3.1: lithium hydroxide / tetrahydrofuran; ethanol / 2 h / 50 °C

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3486242, 2019, A1
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - US2021/122714, 2021, A1

86
[ 7580-85-0 ]
4-(4-(tert-butoxy)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxypyridine-1(2H)-yl)butyrylamino)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2,6-dimethylpyridine / dichloromethane / 2 h / 30 °C / Cooling with ice 2: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C 3: lithium hydroxide / ethanol; tetrahydrofuran / 2 h / 50 °C 4: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 2 h / 80 °C
	Multi-step reaction with 4 steps 1.1: 2,6-dimethylpyridine / dichloromethane / Cooling with ice 1.2: 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran; water / 2 h / -78 °C 3.1: lithium hydroxide / tetrahydrofuran; ethanol / 2 h / 50 °C 4.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / ethyl acetate / 2 h / 80 °C

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3486242, 2019, A1
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - US2021/122714, 2021, A1

87
[ 7580-85-0 ]
[ 32779-36-5 ]
5-bromo-2-(2-(tert-butoxy)ethoxy)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃;	182 5-Bromo-2-(2-(tert-butoxy)ethoxy)pyrimidine A solution of 2-(tert-butoxy)ethan-1-ol (92 mg, 0.775 mmol) and 5-bromo-2-chloropyrimidine (150 mg, 0.775 mmol) in THF (2.6 mL) was cooled to 0 °C. Sodium hydride 60% in oil (33.5 mg, 0.8525 mmol) was added and the reaction was stirred for 1 hour at 0 °C before allowing to warm to ambient temperature overnight. The volatiles were removed in vacuo and the reaction mixture was diluted with H2O (5 mL), and extracted with DCM (3 x 5 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The filtrate was then adsorbed onto celite and purified by silica gel chromatography to provide the title compound as a solid (61.2 mg, 0.222 mmol, 29% yield).1H NMR (400 MHz, CHLOROFORM-d) δppm 8.52 (s, 2 H), 4.45 (m, 2 H), 3.73 (m, 2 H), 1.22 (s, 9 H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/109647, 2018, A1 Location in patent: Page/Page column 356

88
[ 7580-85-0 ]
methyl 5-formyl-4-hydroxy-2-methoxybenzoate [ No CAS ]
methyl 4-(2-(tert-butoxy)ethoxy)-5-formyl-2-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With 2-(diphenylphosphino)pyridine; di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 4h;

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2019, vol. 21, # 19, p. 7763 - 7767]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	7580-85-0	MDL No. :	MFCD00059004
Formula :	C₆H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BDLXTDLGTWNUFM-UHFFFAOYSA-N
M.W :	118.17	Pubchem ID :	24232
Synonyms :

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.24
TPSA :	29.46 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.74 cm/s

[ CAS No. 7580-85-0 ] {[proInfo.proName]}

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Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 7580-85-0 ]

[ 7580-85-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 7580-85-0 ]

Ethers

Alcohols

Precautionary Statements-General

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Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	0.39
Log Po/w (WLOGP) :	0.79
Log Po/w (MLOGP) :	0.61
Log Po/w (SILICOS-IT) :	0.6
Consensus Log Po/w :	0.88

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-0.62
Solubility :	28.3 mg/ml ; 0.24 mol/l
Class :	Very soluble
Log S (Ali) :	-0.57
Solubility :	31.5 mg/ml ; 0.266 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.01
Solubility :	11.4 mg/ml ; 0.0968 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Signal Word:	Danger	Class:	3
Precautionary Statements:	P501-P260-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P314-P303+P361+P353-P304+P340+P312-P403+P233-P403+P235-P405	UN#:	3271
Hazard Statements:	H372-H336-H226	Packing Group:	Ⅲ
GHS Pictogram:

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P378
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 7580-85-0 ] {[proInfo.proName]}

Quality Control of [ 7580-85-0 ]

Related Doc. of [ 7580-85-0 ]

Product Details of [ 7580-85-0 ]

Calculated chemistry of [ 7580-85-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7580-85-0 ]

Application In Synthesis of [ 7580-85-0 ]

[ 7580-85-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 7580-85-0 ]

Ethers

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

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[ 7580-85-0 ]