[ CAS No. 1122-58-3 ] {[proInfo.proName]}

Name: 1122-58-3|4-Dimethylaminopyridine|98%
Brand: Ambeed
SKU: A538667
Price: 6.0 USD
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Quality Control of [ 1122-58-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1122-58-3 ]

CAS No. :	1122-58-3	MDL No. :	MFCD00006418
Formula :	C₇H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VHYFNPMBLIVWCW-UHFFFAOYSA-N
M.W :	122.17	Pubchem ID :	14284
Synonyms :

Calculated chemistry of [ 1122-58-3 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.44
TPSA :	16.13 Å²

Pharmacokinetics

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) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.53
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.49
Log Po/w (SILICOS-IT) :	0.9
Consensus Log Po/w :	1.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.87
Solubility :	1.65 mg/ml ; 0.0135 mol/l
Class :	Very soluble
Log S (Ali) :	-1.28
Solubility :	6.4 mg/ml ; 0.0524 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.09
Solubility :	0.995 mg/ml ; 0.00815 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 1122-58-3 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P260-P262-P264-P270-P271-P273-P280-P301+P310+P330-P302+P352+P310-P304+P340+P311-P305+P351+P338+P310-P308+P311-P332+P313-P361+P364-P391-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301+H331-H310-H315-H318-H370-H411	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1122-58-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1122-58-3 ]
Downstream synthetic route of [ 1122-58-3 ]

[ 1122-58-3 ] Synthesis Path-Upstream 1~15

1
[ 1122-58-3 ]
[ 50533-97-6 ]

Reference： [1] New Journal of Chemistry, 2008, vol. 32, # 6, p. 1027 - 1037

2
[ 75-44-5 ]
[ 1122-58-3 ]
[ 1193-24-4 ]
[ 1193-21-1 ]

Reference： [1] Patent: US5750694, 1998, A,

3
[ 1122-58-3 ]
[ 84539-35-5 ]

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[2] Tetrahedron Letters, 2006, vol. 47, # 49, p. 8693 - 8697
[3] Green Chemistry, 2018, vol. 20, # 19, p. 4448 - 4452
[4] Synthetic Communications, 2009, vol. 39, # 2, p. 215 - 219
[5] Tetrahedron Letters, 1997, vol. 38, # 25, p. 4415 - 4416
[6] Heterocycles, 1987, vol. 26, # 11, p. 2905 - 2910
[7] Chemical Communications, 2006, # 25, p. 2673 - 2674
[8] Journal of the American Chemical Society, 2017, vol. 139, # 7, p. 2557 - 2560
[9] Angewandte Chemie - International Edition, 2017, vol. 56, # 45, p. 14272 - 14276
[10] Tetrahedron Letters, 2008, vol. 49, # 1, p. 189 - 194

4
[ 1122-58-3 ]
[ 84539-35-5 ]
[ 139111-73-2 ]

Reference： [1] Russian Journal of General Chemistry, 2009, vol. 79, # 5, p. 911 - 918

5
[ 1122-58-3 ]
[ 109-97-7 ]
[ 100-36-7 ]
[ 5176-27-2 ]

Reference： [1] Patent: US5574017, 1996, A,

6
[ 1122-58-3 ]
[ 163685-01-6 ]
[ 491-11-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1996, # 8, p. 1553 - 1558

7
[ 1122-58-3 ]
[ 1801-10-1 ]

Reference： [1] Patent: US6441233, 2002, B1,

8
[ 113399-37-4 ]
[ 1122-58-3 ]
[ 63710-33-8 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 742 - 746[2] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 4, p. 821 - 825
[3] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 742 - 746[4] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 4, p. 821 - 825

9
[ 1122-58-3 ]
[ 4389-45-1 ]
[ 503-38-8 ]
[ 22223-49-0 ]

Reference： [1] Patent: US5962436, 1999, A,

10
[ 1122-58-3 ]
[ 7417-18-7 ]
[ 124-63-0 ]
[ 121-44-8 ]
[ 36449-75-9 ]

Reference： [1] Patent: US6100293, 2000, A,

11
[ 1122-58-3 ]
[ 5419-55-6 ]
[ 402-43-7 ]
[ 23287-26-5 ]
[ 145797-53-1 ]
[ 128796-39-4 ]

Reference： [1] Patent: US2003/109700, 2003, A1,
[2] Patent: US6197798, 2001, B1,

12
[ 1122-58-3 ]
[ 84358-13-4 ]

Reference： [1] Patent: US6127422, 2000, A,
[2] Patent: EP806411, 1997, A2,

13
[ 1122-58-3 ]
[ 3144-09-0 ]
[ 24424-99-5 ]
[ 121-44-8 ]
[ 147751-16-4 ]

Reference： [1] Patent: US6358981, 2002, B1, . Location in patent: Page column 22

14
[ 1122-58-3 ]
[ 396092-82-3 ]

Reference： [1] Journal of Organic Chemistry, 2002, vol. 67, # 1, p. 238 - 241
[2] Chemistry - A European Journal, 2017, vol. 23, # 16, p. 3837 - 3849
[3] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6622 - 6625
[4] Inorganic Chemistry, 2017, vol. 56, # 14, p. 8244 - 8256
[5] Patent: US2011/301148, 2011, A1, . Location in patent: Page/Page column 7
[6] Organic and Biomolecular Chemistry, 2013, vol. 11, # 46, p. 8073 - 8081

15
[ 1122-58-3 ]
[ 24424-99-5 ]
[ 69684-69-1 ]
[ 255882-72-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In dichloromethane	To a solution of azetidine-2(S)-carboxylic acid, methyl ester hydrochloride salt (6.6 mmol, 1.0 g) in anhydrous dichloromethane (14 mL) was added di-tert-butyl dicarbonate (1.05 equiv; 6.9 mmol, 1.51 g), triethylamine (3.0 equiv; 19.8 mmol, 2.0 g, 2.76 mL), and 4-dimethyl-aminopyridine in that order at 25° C. Evolution of gas was observed almost immediately and the reaction mixture became cloudy. After stirring overnight (15 h) it was diluted with ethyl acetate and washed with 1N hydrochloric acid, saturated bicarbonate solution, and brine. Drying (MgSO₄), filtration, and concentration afforded N-(tert-butyloxycarbonyl)-azetidine-2(S)-carboxylic acid, methyl ester as a pale yellow oil (1.24 g, 87percent yield) of satisfactory purity. ¹H NMR (400 MHz, CDCl₃): δ 4.63 (dd, 1H, J=9.2, 5.2 Hz), 4.05 (m, 1H), 3.89 (m, 1H), 3.79 (s, 3H), 2.51 (m, 1H), 2.18 (m, 1H), 1.43 (s, 9H).

Reference： [1] Patent: US6645939, 2003, B1,

[ 1122-58-3 ] Synthesis Path-Downstream 1~88

1
[ 590-92-1 ]
[ 1122-58-3 ]
[ 89389-94-6 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6516 - 6521

2
[ 1122-58-3 ]
[ 13509-27-8 ]
Phenolate₄-dimethylamino-1-methoxycarbonyl-pyridinium; [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 906 - 910

3
[ 1122-58-3 ]
[ 27607-77-8 ]
[ 29261-33-4 ]
C₂₆H₂₀F₂N₈⁽²⁺⁾*C₇H₁₀N₂*2CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Chemistry Letters,1993,p. 517 - 520

4
[ 1122-58-3 ]
[ 4232-27-3 ]
[ 28767-46-6 ]
[ 20350-26-9 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5072 - 5077

5
[ 1122-58-3 ]
[ 4232-27-3 ]
2,4-Dinitro-phenolate1-acetyl-4-dimethylamino-pyridinium; [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 906 - 910

6
[ 113399-37-4 ]
[ 1122-58-3 ]
[ 63710-33-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 742 - 746
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 821 - 825
[2]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 742 - 746
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 821 - 825

7
[ 1122-58-3 ]
[ 163685-01-6 ]
[ 491-11-2 ]
1-(4,6-Dimethoxy-[1,3,5]triazin-2-yl)-4-dimethylamino-pyridinium [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1996,p. 1553 - 1558

8
[ 1122-58-3 ]
[ 1780-40-1 ]
5-chloro-2,6-bis[4-(dimethylamino)pyridino]pyrimidin-4-olate chloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 4636 - 4644

9
[ 1122-58-3 ]
[ 1780-40-1 ]
C₁₈H₂₀ClN₆O⁽¹⁺⁾*HI*I^(1-) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 4636 - 4644

10
[ 108-30-5 ]
[ 1122-58-3 ]
[ 3056-17-5 ]
1/2 4-N,N-dimethylaminopyridinium salt of 3'-deoxy-2',3'-didehydrothymidine monosuccinic ester [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1998,vol. 17,p. 2127 - 2133

11
[ 108-30-5 ]
[ 1122-58-3 ]
[ 3056-17-5 ]
stavudine 5'-monosuccinate 4-dimethylaminopyridinium salt [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2001,vol. 35,p. 134 - 138

12
[ 1122-58-3 ]
[ 4263-52-9 ]
2-(4-dimethylamino-1-pyridinium)-1-ethanesulfonate [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 781 - 782

13
[ 1122-58-3 ]
[ 396092-82-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 12.6 mL (125 mmol) of N,N-dimethylethanolamine in 160 mL of anhydrous hexane are added, under an argon atmosphere, at -5 C., over 2 hours 30 minutes, 100 mL (250 mmol) of 2.5 M n-butyllithium in hexane, and the reaction medium is then stirred for 30 minutes at 0 C., followed by addition of 7.6 g (62.5 mmol) of 4-dimethylaminopyridine. After stirring for 1 hour at 0 C., the reaction medium is cooled to -78 C. and 51.8 g (156.2 mmol) of carbon tetrabromide dissolved in 250 mL of anhydrous hexane are added over 2 hours 30 minutes at -78 C. The temperature is allowed to rise to 0 C. and stirring is then continued for 1 hour 30 minutes.The medium is then hydrolysed with water (400 mL) and subsequently extracted with Et2O (400 mL) and DCM (2*400 mL). The combined organic phases are dried over Na2SO4, filtered and concentrated under reduced pressure. 6.4 g of 2-bromo-N,N-dimethylpyridin-4-amine are obtained in the form of a brown solid, which is used without further purification in the following step.Yield=51%1H NMR, (CDCl3, 400 MHz, delta (ppm): 7.9 (d, 1H); 6.6 (s, 1H); 6.4 (d, 1H); 2.9 (s, 6H).

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 238 - 241
[2]Chemistry - A European Journal,2017,vol. 23,p. 3837 - 3849
[3]Tetrahedron Letters,2010,vol. 51,p. 6622 - 6625
[4]Inorganic Chemistry,2017,vol. 56,p. 8244 - 8256
[5]Patent: US2011/301148,2011,A1 .Location in patent: Page/Page column 7
[6]Organic and Biomolecular Chemistry,2013,vol. 11,p. 8073 - 8081

14
[ 1122-58-3 ]
[ 1780-40-1 ]
[ 143-66-8 ]
C₂₅H₃₀ClN₈⁽³⁺⁾*3C₂₄H₂₀B^(1-) [ No CAS ]

Reference： [1]Heterocycles,2002,vol. 57,p. 615 - 621

15
[ 1122-58-3 ]
[ 28969-60-0 ]
[ 143-66-8 ]
1,1'-(6-amino-5-chloropyrimidine-2,4-diyl)-bis-[4-(dimethylamino)pyridinium] bis(tetraphenylborate) [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 949 - 956

16
[ 1122-58-3 ]
[ 28969-60-0 ]
1,1'-(6-amino-5-chloropyrimidine-2,4-diyl)-bis-[4-(dimethylamino)pyridinium] dichloride [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 949 - 956

17
[ 1122-58-3 ]
[ 434935-69-0 ]
[ 625-45-6 ]
[ 19500-95-9 ]
C₁₁H₁₁NO₆ [ No CAS ]
(1-methoxyacetyl-1<i>H</i>-pyridin-4-ylidene)-dimethyl-ammonium; 2-methyl-6-nitro-benzoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 1822 - 1830

18
[ 1122-58-3 ]
[ 2402-79-1 ]
1,1'-bis[4-dimethylamino-(3,5-dichloro-pyridine-2,6-diyl)pyridinium]dichloride [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 1667 - 1674

19
[ 1122-58-3 ]
[ 1780-40-1 ]
[ 27607-77-8 ]
(5-chloropyrimidine-2,4,6-triyl)-1,1',1''-tris[4-(dimethylamino)pyridinium] tris(trifluoromethanesulfonate) [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2006,vol. 61,p. 396 - 405

20
[ 1122-58-3 ]
[ 1780-40-1 ]
(5-chloropyrimidine-2,4,6-triyl)-1,1',1''-tris[4-(dimethylamino)pyridinium] trichloride [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2006,vol. 61,p. 396 - 405

21
[ 1122-58-3 ]
[ 27607-77-8 ]
[ 652-36-8 ]
1,2,4,5-tetrakis[4-(dimethylamino)-1-pyridinio]benzene tetrakis(trifluoromethanesulfonate) [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 1002 - 1007

22
[ 1122-58-3 ]
[ 3144-09-0 ]
[ 24424-99-5 ]
[ 121-44-8 ]
[ 147751-16-4 ]

Reference： [1]Patent: US6358981,2002,B1 .Location in patent: Page column 22

23
[ 1122-58-3 ]
[ 32707-89-4 ]
[ 538-75-0 ]
[ 2243-42-7 ]
2-Phenoxy-benzoic acid 3,5-bis-trifluoromethyl-benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	In dichloromethane; at 0 - 20℃;	EXAMPLE 13 2-Phenoxy-benzoic acid 3,5-bis-trifluoromethyl-benzyl ester To a solution of 118 mg (0.55 mmol) 2-phenoxybenzoic acid and 122 mg (0.50 mmol) 3,5 bis(trifluoromethyl)benzyl alcohol in 1.5 ml dichloromethane at 0 C. was added a solution of 124 mg (0.60 mmol) 1,3-dicyclohexylcarbodiimide and 7 mg (0.06 mmol) 4-dimethylaminopyridine in 1 ml dichloromethane.. The ice bath was removed and stirring was continued at room temperature overnight.. The solvent was removed in vacuo and the residue re-dissolved in diethyl ether, filtered and evaporated.. The residue was purified by flash chromatography to give 70 mg (32%) of the title compound as white crystals. MS m/e (%): 440 (M+, 51), 347 (39), 227 (36), 197 (100).

Reference： [1]Patent: US6407111,2002,B1 .Location in patent: Page column 24

24
[ 1122-58-3 ]
[ 34619-03-9 ]
[ 113305-94-5 ]
[ 710322-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,-tetramethylethylenediamine; In 1,4-dioxane; at 25℃; for 20h;	A solution of <strong>[113305-94-5]2-amino-5-cyanopyrazine</strong> (500.0 mg, 4.162 mmol) in 1,4- dioxane (8.3 ML) was treated with 4- (dimethylamino) pyridine (305.1 mg, 2.497 mmol), N, N, N', N'-TETRAMETHYLETHYLENEDIAMINE (241.8 mg, 2.081 mmol), and di-tert-butyl dicarbonate (2.9 mL, 12.49 mmol). The reaction stirred at 25C for 20 h and then was concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 10% ethyl acetate/hexanes) afforded 5- [ [BIS [ (L, 1-dimethylethoxy) carbonyl] ] amino]-2- pyrazinecarbonitrile as a white solid: mp 67-68C ; (ES) +-HRMS m/e calcd for CISH2ON404 (M+Na) + 343. 1377, found 343.1379.

Reference： [1]Patent: WO2004/52869,2004,A1 .Location in patent: Page 76

25
[ 1122-58-3 ]
[ 118-12-7 ]
[ 63857-00-1 ]
2-[2-[2-(4-dimethylaminopyridinium)-3-[2-(1,3-dihydro-1,3,3-trimethyl-2H-indole-2-ylidene)-ethylidene]-1-cyclohexene-1-yl]-ethenyl]-1,3,3-trimethyl-3H-indolium dichloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		3.6 g 4-dimethylaminopyridine and 11. 8 g dye A (both available from Aldrich) were added under stirring to 60 ml Downanol PM in a 0. 5 1 three-necked flask equipped with a stirrer and a reflux condenser. Then 11.8 g 2-methylene-1, 3,3-trimethylindoline (Fischer base, available from Aldrich) was added under stirring for one minute to this suspension. The reaction mixture was heated to 80C for 2 hours. Then the reaction mixture was left to cool to room temperature and 200 ml of a 1 wt. -% hydrochloric acid were added. After the reaction mixture had cooled to room temperature, the insoluble portion was separated by filtration and washed with 0.5 1 of water. Then the product was dried for one day at 50C in a circulating air oven. Yield: 15.6 g (81.0 % based on dye A). The dried product was suspended in 150 ml methyl ethyl ketone and heated to 80C for one hour. Subsequently, the solution with a temperature of about 40C was filtered and the solid portion was washed with ethyl acetate. The product was air-dried. The yield after clean-up WAS 78 WT. -%; UV/VIS SPECTRUM IN METHANOL : 786 NM, EXTINCTION COEFFICIENT E = 381 1/G X CM.

Reference： [1]Patent: WO2004/52995,2004,A1 .Location in patent: Page 23

26
[ 1122-58-3 ]
4-(4-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid [ No CAS ]
[ 41748-71-4 ]
4-(4-bromo-2-methoxyphenyl)-2-hydroxy-N-(1H-indazol-4-yl)-4-methyl-2-(trifluoromethyl)pentanoic acid amide [ No CAS ]

Reference： [1]Patent: WO2005/3098,2005,A1 .Location in patent: Page/Page column 42

27
[ 1122-58-3 ]
1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) [ No CAS ]
[ 3025-95-4 ]
[ 107-19-7 ]
[ 479200-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; triethylamine; In tetrahydrofuran;	Example 20 Preparation of N-Acetyl-beta-alanine Propargyl Ester(4b) To a solution of N-Acetyl-beta-alanine(4a) in THF (20 mL) was added propargyl alcohol (840 mg, 15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (1.035 g,5.39 mmol), triethylamine (540 mg, 5.4 mmol) and 4-dimethylaminopyridin (5 mg). The reaction mixture was stirred at room temperature for 2 d. The reaction mixture was poured into EtOAc (100 mL), washed with NaH2PO4 (50% sat. aq, 2*50 mL) followed by NaHCO3 (50% sat. aq, 50 mL). After drying (Na2SO4), EtOAc was removed under reduced pressure to leave a colourless oil that solidified on standing. Product yield 536 mg, 59%.

Reference： [1]Patent: US2003/143561,2003,A1

28
[ 1122-58-3 ]
[ 1701-57-1 ]
[ 73831-13-7 ]
[ 335155-20-9 ]

Yield	Reaction Conditions	Operation in experiment
1.10 g (70%)	With triethylamine; In dichloromethane;	1A. 2-Methyl-4-((2,3,4,5-tetrahydro-1H-benzo[b]azepine)-1-carbonyl)-benzonitrile To a solution of 2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.80 g, 5.44 mmol) in dichloromethane (50 ml) were added 4cyano-3methylbenzoic acid (0.96 g, 5.95 mmol), triethylamine (0.60 g, 5.95 mmol), 4(dimethylamino)pyridine (0.73 g, 5.95 mmol) and WSCDI (1.24 g, 6.48 mmol). The mixture was stirred at reflux for 18 h, cooled and evaporated in vacua. The residue was partitioned between EtOAc and 1M KHSO4. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated in vacuo. The crude material was purified by flash chromatography on silica (eluant EtOAc:pet. ether 30:70); yield 1.10 g (70%).

Reference： [1]Patent: US2003/87892,2003,A1

29
[ 1122-58-3 ]
[ 76-83-5 ]
[ 48149-72-0 ]
[ 258854-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In pyridine; water;	Route b: 1-O-(2-propenyl)-6-O-triphenylmethyl-alpha-D-galactose (III) The Compound (II)(11.1 g, 50.2 mmol) was dissolved in 50 mL of anhydrous pyridine. To the solution, 16.8 g (60.2 mmol) of tritylchloride and 614 mg (5.02 mmol) of p-dimethylaminopyridine (DMAP) were added. The mixture was allowed to react for 24 hours at 40 C. while stirring. Then, the reaction was quenched by addition of 100 mL of cold water, and then extracted with ethyl acetate (3200 mL). The organic layers were combined, neutralized to pH 4 with 1.0N hydrochloric acid, washed with brine (2200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel flash chromatography (chloroform: methanol=20:1?15:1) to give a pale yellowish oily substance (yield:21.3 g, 46.1 mmol, recovery 91.8%). [alpha]D=+64.2 (c 1.48, CHCl3)

Reference： [1]Patent: US2002/28777,2002,A1

30
[ 1122-58-3 ]
[ 6638-79-5 ]
[ 154775-43-6 ]
[ 301186-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane;	Step B 1-(tert-Butoxycarbonyl)-4-(3-(4-fluorophenyl)-3-oxopropyl)piperidine Molecular sieve pellets (4 A), N,O-dimethylhydroxylamine hydrochloride (227 mg, 3.32 mmol), and DIEA (0.41 mL, 0.30 g, 2.4 mmol) were added to a solution of 3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionic acid (500 mg, 1.94 mmol, from Step A) in 1,4-dioxane (10 mL). 4-(Dimethylamino)pyridine (57 mg, 0.47 mmol) and EDC (483 mg, 2.52 mmol) were added and the mixture was stirred for 16 h at rt. The mixture was partitioned between EtOAc (50 mL) and 1 N aq. HCl (50 mL). The aqueous layer was extracted with EtOAc (50 mL). The organic layers were washed with sat'd NaCl (30 mL), dried (Na2SO4), decanted, and evaporated to give 583 mg of N-methoxy-N-methyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionamide.

Reference： [1]Patent: US6399619,2002,B1

31
[ 1122-58-3 ]
[ 1801-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tributyl-amine;	EXAMPLE 7 Preparation of 3-(trifluoromethyl)-benzoic Acid Amide The process is carried out analogously to example 3, but adding 0.431 g of 4-dimethylamino-pyridine and 7.11 g of tributylamine. The yield of title compound is 96% by weight.

Reference： [1]Patent: US6441233,2002,B1

32
[ 1122-58-3 ]
[ 75-36-5 ]
[ 79-06-1 ]
[ 628-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In tetrahydrofuran;	EXAMPLE 2 21.3 g of acrylamide (0.3M), 0.5 g 4-(dimethylamino)-pyridine and 24.2 ml (0.3M) pyridine was dissolved in 800 ml HPLC grade THF. The reaction mixture was stirred at 10 C. to obtain a clear solution. Then 21.3 ml (0.3M) acetyl chloride in 22 ml THF was added dropwise to the above reaction mixture over 1 hour. After the addition of acetyl chloride was over, a sticky yellow precipitate of pyridine -HCl was obtained. This precipitate was filtered under vacuum to obtain a clear THF solution, which was then concentrated under vacuum at 40 C. to obtain a semisolid mass. This was precipitated in petroleum ether to get a low melting semisolid product (acetylacrylamide). The polymerisation comprising this monomer was carried out at follows: 0.238 g (0.07M) NIPAM and 0.102 g (0.03M) acetylacrylamide were dissolved in 30 m of water taken in a round flask.

Reference： [1]Patent: US6605714,2003,B2

33
[ 1122-58-3 ]
[ 24424-99-5 ]
[ 69684-69-1 ]
[ 255882-72-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine; In dichloromethane;	To a solution of azetidine-2(S)-carboxylic acid, methyl ester hydrochloride salt (6.6 mmol, 1.0 g) in anhydrous dichloromethane (14 mL) was added di-tert-butyl dicarbonate (1.05 equiv; 6.9 mmol, 1.51 g), triethylamine (3.0 equiv; 19.8 mmol, 2.0 g, 2.76 mL), and 4-dimethyl-aminopyridine in that order at 25 C. Evolution of gas was observed almost immediately and the reaction mixture became cloudy. After stirring overnight (15 h) it was diluted with ethyl acetate and washed with 1N hydrochloric acid, saturated bicarbonate solution, and brine. Drying (MgSO4), filtration, and concentration afforded N-(tert-butyloxycarbonyl)-azetidine-2(S)-carboxylic acid, methyl ester as a pale yellow oil (1.24 g, 87% yield) of satisfactory purity. 1H NMR (400 MHz, CDCl3): delta 4.63 (dd, 1H, J=9.2, 5.2 Hz), 4.05 (m, 1H), 3.89 (m, 1H), 3.79 (s, 3H), 2.51 (m, 1H), 2.18 (m, 1H), 1.43 (s, 9H).

Reference： [1]Patent: US6645939,2003,B1

34
[ 1122-58-3 ]
[ 59281-14-0 ]
[ 76-83-5 ]
[ 166742-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; methanol;	REFERENCE EXAMPLE 47 4-Dimethylaminopyridine (17.55 g) and trityl chloride (40.5 g) are added to a solution of 5-benzyloxy-2-hydroxymethyl-4-pyridone (30.2 g) in dry dimethylformamide and the mixture stirred and heated at 95 C. for 2 hours. After cooling the mixture is poured into iced-water (800 mL) and the precipitate collected, washed with water (2500 mL) and sucked dry. The solid is boiled with methanol (500 mL) and after cooling the solid is collected, washed with methanol (200 mL) and diethyl ether (2100 mL) and dried at 80 C. to give 5-benzyloxy-2-trityloxymethyl-4-pyridone (26.5 g) as a white solid, m.p. 233-5 C.

Reference： [1]Patent: US6472412,2002,B1

35
[ 109-02-4 ]
[ 1122-58-3 ]
[ 24424-99-5 ]
[ 55516-54-6 ]
[ 55447-00-2 ]

Yield	Reaction Conditions	Operation in experiment
	In hydrogenchloride; methanol; dichloromethane; toluene;	EXAMPLE 14 N-[N-[N-(4-(piperidin-4-yl)butanoyl)-N-ethylglycyl]aspartyl]-L-beta-decahydronaphth-1-yl alanine STR19 A. beta-(1-naphthyl)alanine (2.0 g) is stirred in a saturated hydrogen chloride/methanol solution for about 2 hours at room temperature. The mixture is evaporated in vacuo and toluene azeotroped twice from the residue. The residue is suspended in methylene chloride, N-methyl morpholine (1.02 ml) added, and the mixture cooled to 0° C. Di-tert-butyl dicarbonate (2.02 g) and 4-dimethylaminopyridine (DMAP) (0.8g) are added, the solution allowed to warm to room temperature, and stirredat room temperature for about 2 hours. The mixture is washed with 5percent HCl, water, dried over sodium sulfate, filtered, and evaporated in vacuo to give N-BOC-beta-(1 -naphthyl)alanine, methyl ester.

Reference： [1]Patent: US5866685,1999,A

36
[ 1122-58-3 ]
[ 6684-06-6 ]
[ 89464-87-9 ]
2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane;	(i) 4-Dimethylaminopyridine (0.1 g) was added to a solution of 2-chloropyridine-3-sulphonyl chloride (1.06 g), <strong>[89464-87-9]2-amino-3-methoxy-5-methylpyrazine</strong> (0.695 g) and pyridine (0.424 ml) in dichloromethane (5 ml) and the mixture was stirred at ambient temperature for 18 hours. The solution was then transferred to a silica gel Mega Bond Elut column. Elution with 0-40% ethyl acetate/hexane gave 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.47 g) as an oil; 1 H NMR (d6 -DMSO): 2.3 (s, 3 H), 3.9 (s, 3 H), 7.5 (s, 1 H), 7.65 (dd, 1 H), 8.45 (dd, 1 H), 8.7 (dd, 1 H); mass spectrum (+ve CI): 315 (M+H)+.

Reference： [1]Patent: US5866568,1999,A

37
[ 1122-58-3 ]
[ 7417-18-7 ]
[ 124-63-0 ]
[ 121-44-8 ]
[ 36449-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium bromide; In dichloromethane; acetone;	Step A Preparation of 2-tetrahydropyranyloxyphenyl ethyl bromide STR83 A solution of <strong>[7417-18-7]2-methoxyphenethyl alcohol</strong> (5.0 g, 32.6 mmol) in 40 ml of CH2 Cl2 was added dimethylaminopyridine (DMAP) (10 mg), Et3 N (11.4 ml, 81.8 mmol) and MsCl (5.05 ml, 65.2 mmol) at 0 C. After 1 h, the reaction mixture was poured into hexane and it was washed with NaHCO3 (2*), water and dried with MgSO4. Upon removal of solvents, the residue was dissolved in 50 ml of acetone and to the solution was added LiBr (11.34 g, 130.6 mmol). After the solution was heated at reflux for 16 h, it was poured into ether and washed with water, dried with MgSO4, filtered and dried to afford 2-methoxyphenethyl bromide.

Reference： [1]Patent: US6100293,2000,A

38
[ 1122-58-3 ]
[ 4389-45-1 ]
[ 503-38-8 ]
[ 22223-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; N-methyl-acetamide; methanol;	Step A Preparation of methyl 2-amino-3-methylbenzoate To a solution of 2-amino-3-methylbenzoic acid (25.0 g, 165 mmol) in p-dioxane (43 mL) under a nitrogen atmosphere was added diphosgene (20 mL, 165 mmol) and the resulting solution was stirred at 60 C. overnight. After cooling to room temperature, the mixture was filtered and the precipitate was rinsed with hexanes and dried in vacuo to afford 28.49 g of an off white solid. Without further characterization, this material was suspended in dry dimethylformamide (320 mL) and methanol (11.7 mL). 4-Dimethylaminopyridine (3.9 g) was added to this suspension and the resulting solution was stirred at 60 C. for 2 days. The cooled reaction mixture was diluted with saturated sodium bicarbonate solution and saturated ammonium chloride solution and extracted three times with ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated under reduced pressure to yield the title compound of Step A (25.40 g) as an oil. 1 H NMR (CDCl3): delta 7.73 (d, 1H), 7.10 (d, 1H), 6.52 (dd,1H), 5.85 (br s,2H), 3.80 (s,3H), 2.07 (s,3H). This material was used in Step B without further characterization.

Reference： [1]Patent: US5962436,1999,A

39
[ 1122-58-3 ]
[ 6338-41-6 ]
[ 90345-66-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; acetic anhydride; In dichloromethane; toluene;	(a) 5-Acetoxymethylfuran-2-carboxylic acid A mixture of 5-hydroxymethylfuran-2-carboxylic acid (5.90 g), dry dichloromethane (100 ml), pyridine (6.71 ml), 4-dimethyl-aminopyridine (507 mg), and acetic anhydride (4.21 ml) was stirred for 2 hours at room temperature. The mixture was diluted with ethyl acetate and washed with 5M hydrochloric acid and brine (3 times), dried (MgSO4), and evaporated. The residue was re-evaporated twice from dry toluene to give the title acid as a solid (5.00 g); deltaH [(CD3)2 CO) 2.05 (3 H, s), 5.11 (2 H, s), 6.62 (1 H, d, J 4 Hz), 7.17 (1 H, d, J 4 Hz) and 8.31 (1 H, br s).

Reference： [1]Patent: US6001997,1999,A

40
[ 1122-58-3 ]
[ 76-83-5 ]
[ 491-19-0 ]
[ 140694-90-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine; In hexane; ethyl acetate; N,N-dimethyl-formamide;	A. [2R-(2alpha,3beta,4beta)]Tetrahydro-2-[(triphenylmethoxy)methyl]-3,4-furandiol Triethylamine (7.8 ml. 55 mmol), trityl chloride (12.48 g, 44.8 mmol) and 4-dimethyaminopyridine (0.228 g., 1.87 mmol) were added in succession to a stirred solution of 5 g. (37.3 mmol) <strong>[491-19-0]1,4-anhydro-D-ribitol</strong> (Chem. Ber. 1952, 85, 1000-1007) in 45 ml. anhydrous dimethyl formamide. The resulting mixture was stirred at ambient temperature for 3 hours, warmed to 55 C. and stirred at that temperature for 5 hours. 1 H NMR of an aliquot showed complete transformation of the starting material to the product. The reaction mixture was diluted with 300 ml methylene chloride and washed with water (3*200 ml.). The organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude residue was subjected to flash chromatography (silica gel/eluted with hexane to 50% ethyl acetate in hexane, and finally 100% ethyl acetate) affording 7.1 g. (51% yield) of the title compound, [alpha]D =35.5 (c=1, methylene chloride).

Reference： [1]Patent: US5272152,1993,A

41
[ 1122-58-3 ]
[ 496-15-1 ]
[ 16078-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; triethylamine; In chloroform; water;	A 1-Acetylindoline A solution of 11.9 g of indoline in 100 ml of chloroform is cooled to 0 C., 13.9 ml of triethylamine are added and a solution of 10.4 ml of acetic anhydride in 10 ml of chloroform is then added dropwise, followed by 0.1 g of 4-dimethylaminopyride. After stirring for two hours at RT, water is added to the reaction mixture, extraction is carried out with chloroform, the organic phase is dried over sodium sulfate and the solvent is evaporated off under vacuum to give 15.44 g of the expected product, which is used as such.

Reference： [1]Patent: US5594023,1997,A

42
[ 1122-58-3 ]
ethyl acetate n-hexane [ No CAS ]
[ 35677-89-5 ]
(3S)-2-acetoxy-3-(N-benzyloxycarbonylamino)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; diisobutylaluminium hydride; In tetrahydrofuran; water;	EXAMPLE 72 A solution of (S)-3-(N-benzyloxycarbonylamino)tetrahydrofuran-2-one (4.9 g) in tetrahydrofuran (150 ml) was prepared and a toluene solution of diisobutylaluminum hydride (1.5M, 28.0 ml) was added dropwise to the above solution in an argon atmosphere at -70~-65 C. Then, water (5 ml) was added dropwise at the same temperature followed by addition of acetic anhydride (20 ml) and 4-dimethylaminopyridine (DMAP) (0.3 g). After the temperature had risen to room temperature, the reaction mixture was diluted with ethyl acetate (400 ml) and the dilution was stirred at room temperature for 3 hours. The reaction mixture was washed with 1N--HCl, water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in the order mentioned and dried (MgSO4) and the solvent was distilled off. The residue was chromatographed on a silica gel column and elution was carried out with ethyl acetate-hexane (1:1, v/v). From the elude was obtained (3S)-2-acetoxy-3-(N-benzyloxycarbonylamino)tetrahydrofuran as an oil.

Reference： [1]Patent: US5496834,1996,A

43
[ 1122-58-3 ]
[ 1659-31-0 ]
[ 7081-78-9 ]
[ 132201-33-3 ]
[ 216094-54-1 ]
[ 33069-62-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; toluene;	EXAMPLE 35 Taxol The <strong>[132201-33-3]N-benzoyl-(2R,3S)-3-phenylisoserine</strong>, as prepared in Example 34, is treated with 1-chloroethyl ethyl-ether in the presence of a tertiary amine to produce optically pure (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine (2). 7-tri-ethylsilyl baccatin III (1), as synthesised according to Denis et at. (J. Amer. Chem. Soc. 110:5417, 1988), is added to 6 equiv of optically pure (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine (2), 6 equiv of di-2-pyridyl carbonate (DPC), and 2 equiv of 4-(dimethylamino) pyridine (DMAP) in toluene solution (0.02M). This mixture reacts at 73 C. for 100 hours to produce the C-2', C-7-protected taxol derivative (3). Concomitant removal of the protecting groups at C-2' and C-7 in (3) is accomplished with 0.5% HCl in ethanol at 0 C. for 30 hours to produce taxol, whose identity and purity are established via comparison with the melting point, rotation, and spectral (IR, MNR, FABMS) and chromatographic (TLC, HPLC) characteristics of the natural product. STR51

Reference： [1]Patent: US5637739,1997,A

44
[ 1122-58-3 ]
[ 39263-32-6 ]
[ 118578-91-9 ]
[ 133208-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water;	EXAMPLE 1 Preparation of 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide STR6 2-Amino-5-bromobenzonitrile (3.94 g, 20 millimoles), triethylamine (2.22 g, 22 millimoles) and 4-dimethylamino- pyridine (0.49 g, 4 millimoles) were dissolved in 40 ml of dry dichloromethane, to which was slowly added dropwise a solution of 4-diethoxyphosphinoylmethylbenzoyl chloride (5.81 g, 20 millimoles) in 40 ml dry dichloromethane while cooling the system with ice and stirring it. After stirring the resulting mixture at ambient temperature for 10 hours, the reaction mixture was mixed with 50 ml of water and extracted with chloroform. The chloroform layer was dried on anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure. Purification of the residue by a silica gel column chromato-graphy using 1:2 mixture of chloroform and ethyl acetate as an eluent, followed by recrystallization from benzene-n-hexane mixture, gave 2.94 g of 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide as a colorless crystalline product melting at 165-166 C. (after recrystallization from benzene-n-hexane).

Reference： [1]Patent: US5618801,1997,A

45
[ 75-44-5 ]
[ 1122-58-3 ]
[ 1193-24-4 ]
[ 1193-21-1 ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetonitrile;	EXAMPLE 5 To a stirred mixture of <strong>[1193-24-4]4,6-dihydroxypyrimidine</strong> (5.18 g, 1 equivalent) and 4-(N,N,-dimethylamino)pyridine (0.55 g, 0.1 equivalent) in acetonitrile (100 ml) was added phosgene (28 g, 19.7 ml, 6.2 equivalents) in two aliquots. The resulting mixture was stirred for 10 minutes at room temperature and was then stirred for 4 hours at 55 C. The reaction mixture was purged with air after which water (200 ml) was added. The resulting mixture was extracted with dichloromethane (3*100 ml). The organic extracts were combined, washed with water (100 ml), dried over magnesium sulphate and evaporated to dryness to leave 4,6-dichloropyrimidine (4.63 g).

Reference： [1]Patent: US5750694,1998,A

46
[ 1122-58-3 ]
[ 34619-03-9 ]
[ 96042-30-7 ]
[ 2942-42-9 ]
[ 173459-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile;	7-Nitro-1-tert-butoxycarbonyl-indazole A solution of 7-nitro-1H-indazole (2.81 g, 17.23 mmol), di-tertbutyl carbonate (7.52 g, 34.5 mmol), triethylamine (4.81 mL, 34.5 mmol) and 4-dimethylamino-pyridine (2.11 g, 17.2 mmol) in anhydrous acetonitrile (100 mL) is stirred under nitrogen at ambient temperature for approximately 3 hrs. After removing the solvent in vacuo, the residue is partitioned between ethyl acetate and aqueous sodium hydrogen sulfate (1N). The organic layer is separated, washed with saturated aqueous brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by chromatography on flash grade silica gel using DCM. Fractions containing the product are combined, concentrated in vacuo to a solid and dried under high vacuum to provide the title compound as a yellow solid (2.674 g, 10.16 mmol). 1 H NMR (300 MHz, d6-DMSO) delta=1.55 (s, 9H); 7.58 (t, J=8.0 Hz, 1H); 8.20 (d, J=7.4 Hz, 1H); 8.30 (d, J=7.7 Hz, 1H); 8.67 (s, 1H), TLC: Rf =0.5 (DCM).

Reference： [1]Patent: US5795887,1998,A

47
[ 1122-58-3 ]
[ 444-14-4 ]
[ 3282-30-2 ]
[ 114995-48-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; sodium hydrogencarbonate; In diethyl ether; dichloromethane;	(e) N-(2-Bromo-4,6-Difluorophenyl) Pivalamide <strong>[444-14-4]2-Bromo-4,6-difluoroaniline</strong> (10.4 g, Aldrich) was dissolved in dichloromethane (75 ml) and treated with pyridine (4.63 g) in an ice bath. 4-Dimethylaminopyridine (0.61 g) was then added and the mixture was allowed to warn to room temperature. After dropwise addition of pivaloyl chloride (7.23 g, BDH), the reaction was stirred for 5 hours. On completion, the mixture was added to diethyl ether (250 ml), washed twice with 2M HCI (250 ml) and the resulting organic layer was treated with saturated NaHCO3 (2*250 ml). The organic layer was washed with water (250 ml), and dried over MgSO4. Removal of the solvent from the filtrate gave the crude title product as a white solid (13.40 g).

Reference： [1]Patent: US5776951,1998,A

48
[ 1122-58-3 ]
1,2,3,3a,8,8a-hexahydro-5-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole [ No CAS ]
[ 7693-41-6 ]
5-(4-methoxyphenoxycarbonylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;PtO2; In ethyl acetate;	EXAMPLE 10 5-(4-Methoxyphenoxycarbonylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole oxalate 1,2,3,3a,8,8a-Hexahydro-5-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole (3.8 g) was dissolved in ethyl acetate (200 ml) and hydrogenated on a Parr apparatus at 45 psi using PtO2 (380 mg) as a catalyst. The reduction mixture was filtered directly into a nitrogen flushed flask. 4-Dimethylaminopyridine (183 mg) and triethylamine (3.0 g) were added and the mixture cooled to 0 C. before the addition of a solution of <strong>[7693-41-6]4-methoxyphenyl chloroformate</strong> (2.8 g) in ethyl acetate (60 ml) over a period of 1.5 hours. The mixture was washed with water (2*100 ml), dried (Na2 SO4), concentrated and purified by flash chromatography. The pure fractions were concentrated to give 5-(4-methoxyphenoxycarbonylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (1.0 g).

Reference： [1]Patent: US4983616,1991,A

49
[ 1122-58-3 ]
[ 79-37-8 ]
[ 5874-61-3 ]
[ 39608-31-6 ]
[3-(benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; triethylamine; In tetrahydrofuran; pyridine; N-methyl-acetamide; ethyl acetate;	(a) [3-(Benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester N-methyl-N-[(phenylmethoxy)carbonyl]glycine (2.23 g., 10 mmole) is dissolved in 30 ml. of tetrahydrofuran and cooled in an ice-bath. Oxalyl chloride (1 ml., 11.5 mmole) is added followed by 2 drops of dimethylformamide. After stirring for 30 minutes in the ice-bath, the mixture is then stirred at room temperature for an hour. To this 0.25 ml. of oxalyl chloride is added. The mixture is evaporated, redissolved in 15 ml. of tetrahydrofuran, and stirred in an ice bath. A solution of 2-phenyl-4-(phenylmethyl)-5(4H)-oxazolone (3.1 g., 12.4 mmole) dissolved in 15 ml. of tetrahydrofuran is added to the above solution stirring in the ice-bath. Triethylamine (1.4 ml., 10 mmole) is added and the solution is stirred at room temperature overnight. The precipitated triethylamine hydrochloride salt is filtered off. Tetrahydrofuran is removed from the residue and it is then redissolved in pyridine (5 ml.) and p-dimethylamino pyridine (20 mg.) is added. After stirring at room temperature for 3 hours, acetic acid (5 ml.) is added and the reaction mixture is kept at 105 for 30 minutes. The reaction mixture is then evaporated, the residue is dissolved in ethyl acetate, and washed with aqueous sodium bicarbonate and water. After trituration with ethyl acetate/hexane, 2.2 g. of homogeneous [3-(benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester is obtained; m.p. 140-141.
	With acetic acid; triethylamine; In tetrahydrofuran; pyridine; N-methyl-acetamide; ethyl acetate;	(a) [3-(Benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester N-methyl-N-[(phenylmethoxy)carbonyl]glycine (2.23 g., 10 mmole) is dissolved in 30 ml. of tetrahydrofuran and cooled in an ice-bath. Oxalyl chloride (1 ml., 11.5 mmole) is added followed by 2 drops of dimethylformamide. After stirring for 30 minutes in the ice-bath, the mixture is then stirred at room temperature for an hour. To this 0.25 ml. of oxalyl chloride is added. The mixture is evaporated, redissolved in 15 ml. of tetrahydrofuran, and stirred in an ice bath. A solution of 2-phenyl-4-(phenylmethyl)-5(4H)-oxazolone (3.1 g., 12.4 mmole) dissolved in 15 ml. of tetrahydrofuran is added to the above solution stirring in the ice-bath. Triethylamine (1.4 ml., 10 mmole) is added and the solution is stirred at room temperature overnight. The precipitated triethylamine hydrochloride salt is filtered off. Tetrahydrofuran is removed from the residue and it is then redissolved in pyridine (5 ml.) and p-dimethylamino pyridine (20 mg.) is added. After stirring at room temperature for 3 hours, acetic acid (5 ml.) is added and the reaction mixture is kept at 105 for 30 minutes. The reaction mixture is then evaporated, the residue is dissolved in ethyl acetate, and washed with aqueous sodium bicarbonate and water. After trituration with ethyl acetate/hexane, 2.2 g. of homogeneous [3-(benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester is obtained; m.p. 140-141.
	With acetic acid; triethylamine; In tetrahydrofuran; pyridine; N-methyl-acetamide; ethyl acetate;	(c) [3-(Benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester N-methyl-N-[(phenylmethoxy)carbonyl]glycine (2.23 g., 10 mmole) is dissolved in 30 ml. of tetrahydrofuran and cooled in an ice-bath. Oxalyl chloride (1 ml., 11.5 mmole) is added followed by 2 drops of dimethylformamide. After stirring for 30 minutes in the ice-bath, the mixture is then stirred at room temperature for an hour. To this 0.25 ml. of oxalyl chloride is added. The mixture is evaporated, redissolved in 15 ml. of tetrahydrofuran, and stirred in an ice bath. A solution of 2-phenyl-4-(phenylmethyl)-5(4H)-oxazolone (3.1 g., 12.4 mmole) dissolved in 15 ml. of tetrahydrofuran is added to the above solution stirring in the ice-bath. Triethylamine (1.4 ml., 10 mmole) is added and the solution is stirred at room temperature overnight. The precipitated triethylamine hydrochloride salt is filtered off. Tetrahydrofuran is removed from the residue and it is then redissolved in pyridine (5 ml.) and 4-dimethylamino pyridine (20 mg.) is added. After stirring at room temperature for 3 hours, acetic acid (5 ml.) is added and the reaction mixture is kept at 105 for 30 minutes. The reaction mixture is then evaporated, the residue is dissolved in ethyl acetate, and washed with aqueous sodium bicarbonate and water. After trituration with ethyl acetate/hexane, 2.2 g. of homogeneous [3-(benzoylamino)-2-oxo-4-phenylbutyl]methylcarbamic acid, phenylmethyl ester is obtained; m.p. 140-141.

Reference： [1]Patent: US4621092,1986,A
[2]Patent: US4470973,1984,A
[3]Patent: US4514391,1985,A

50
[ 1122-58-3 ]
phenylmethyl ester [ No CAS ]
[ 79-37-8 ]
[ 33560-91-7 ]
[ 27584-70-9 ]
(+/-)-1-[[[3-(benzoylamino)-2-oxo-4-(3-pyridinyl)butyl]methylamino]carbonyl]-L-proline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In tetrahydrofuran; pyridine; N-methyl-acetamide; water; ethyl acetate; triethylamine;	(c) (+-)-1-[[[3-(Benzoylamino)-2-oxo-4-(3-pyridinyl)butyl]methylamino]carbonyl]-L-proline, phenylmethyl ester 2-(benzoylamino)-3-(3-pyridinyl)-propanoic acid (3 g., 9.8 mmole) is suspended in tetrahydrofuran (30 ml.) and while stirring in an ice bath triethylamine (1.4 ml., 10 mmole) and dicyclohexycarbodiimide (2.1 g., 10.2 mmole) are added. The reaction mixture is stirred at room temperature overnight. It is then filtered and the filtrate is evaporated to dryness. This <strong>[27584-70-9]oxazolone</strong> is then dissolved in tetrahydrofuran (15 ml.). 1-[[(2-Carboxyethyl)methylamino]carbonyl]-L-proline, phenylmethyl ester (3 g., 9.4 mmole) is taken into dry tetrahydrofuran and treated with oxalyl chloride and dimethylformamide as set forth in Example 66 (g). The resulting acid chloride is taken into tetrahydrofuran (15 ml.), chilled, and added dropwise to the above <strong>[27584-70-9]oxazolone</strong> tetrahydrofuran solution while stirring in an ice bath. Triethylamine (1.6 ml., 11.4 mmole) is added and the reaction mixture is stirred at room temperature overnight. Triethylamine hydrochloride salt is filtered off and the filtrate is evaporated in vacuo. The concentrated residue is redissolved in pyridine (10 ml.), 4-dimethylamino pyridine (50 mg.) is added, and the solution is stirred at room temperature for 3 hours. Acetic acid (11 ml.) is then added and the reaction mixture is heated at 100 for 40 minutes. It is then evaporated, redissolved in ethyl acetate and extracted with aqueous saturated sodium bicarbonate solution followed by water. The remaining ethyl acetate extract is concentrated and chromatographed over silica gel using the solvent system ethyl acetate:methanol (95:5) to give 0.8 g. of (+-)-1-[[[3-(benzoylamino)-2-oxo-4-(3-pyridinyl)butyl]methylamino]carbonyl]-L-proline, phenylmethyl ester.

Reference： [1]Patent: US4621092,1986,A

51
[ 1122-58-3 ]
[ 24376-01-0 ]
[ 105535-46-4 ]
7β-(N,N-Diethylaminoacetoxy)-8,13-epoxy-6β,9α-dihydroxy-1α-(t-butyldimethylsilyloxy)labd-14-en-11-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; dichloromethane; ethyl acetate;	EXAMPLE 10 7beta-(N,N-Diethylaminoacetoxy)-8,13-epoxy-6beta,9alpha-dihydroxy-1alpha-(t-butyldimethylsilyloxy)labd-14-en-11-one hydrochloride 8,13-Epoxy-6beta,7beta,9alpha-trihydroxy-1alpha-(t-butyldimethylsilyloxy)labd-14-en-11-one (50 mg) was combined with 17.4 mg of <strong>[24376-01-0]N,N-<strong>[24376-01-0]diethylglycine hydrochloride</strong></strong> and 13.1 mg of 4-(N,N-dimethyl amino)pyridine in 2 ml of dry dichloromethane. Dicylohexylcarbodiimide (24 mg) dissolved in 1 ml of dichloromethane was added to the above mixture in a sealed tube. The mixture was allowed to stand at ambient temperature overnight. The dicyclohexylurea was filtered off. After the filtrate was evaporated to dryness, the residue was suspended in ethyl acetate and filtered. The filtrate was flash chromatographed on silica gel in hexan:ethyl acetate (3:1). The appropriate fractions were combined and evaporated to dryness under vacuum. The residue was dissolved in ether, from which the product as the hydrochloride was precipitated, and yielded 32.7 mg of product, mp 200-210. ANALYSIS: Calculated for C32 H58 ClNO7 Si: 60.77% C, 9.26% H, 2.21% N, Found: 60.88% C, 9.68% H, 2.33% N.

Reference： [1]Patent: US4639443,1987,A

52
[ 1122-58-3 ]
[ 13296-04-3 ]
[ 624-83-9 ]
N-methyl-N'-[4-(4-pyridinyl)phenyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform;	EXAMPLE 2 N-Methyl-N'-[4-(4-pyridinyl)phenyl]urea--To 10.52 g. of <strong>[13296-04-3]4-(4-pyridinyl)benzeneamine</strong> suspended in 400 ml. of chloroform was added with stirring 0.76 g. of N,N-dimethyl-4-pyridineamine and 5.5 ml. of methyl isocyanate. The resulting reaction mixture was stirred under reflux for sixteen hours. The reaction mixture was filtered to collect the suspended solid and the filtrate was concentrated in vacuo to yield more solid product plus an oily material. The collected solid was recrystallized from 550 ml. of acetonitrile and dried at 90 C. in vacuo to yield 6.58 g. of N-methyl-N'-[4-(4-pyridinyl)phenyl]urea, m.p. 233-234 C. Another 3.22 g. of this product, m.p. 233-234 C., was obtained by recrystallizing from methanol the above-noted material obtained by concentration of the reaction filtrate.

Reference： [1]Patent: US4376775,1983,A

53
[ 1122-58-3 ]
4,5-diamino-pyrimidine dihydrochloride [ No CAS ]
[ 57479-70-6 ]
[ 77456-49-6 ]
[ 5607-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In pyridine; water;	(a) 4-Amino-5-(4-chloro-2-methoxy-benzoylamino)-pyrimidine The 4-chloro-2-methoxy-benzoyl chloride prepared from 5.6 g of <strong>[57479-70-6]4-chloro-2-methoxy-benzoic acid</strong> and 100 ml of thionyl chloride was dissolved as crude product in 100 ml of pyridine and mixed successively with 5 g of 4,5-diaminopyrimidine dihydrochloride and 1 g of 4-dimethylamino pyridine. After stirring for at first 2 hours at room termperature and then for 1.5 hours at 100 C., the reaction mixture was evaporated to dryness, mixed with water, and neutralized with sodium bicarbonate. The precipitate obtained was used in the next step without further purification. Yield: 5.4 g (65% of theory), M.p.: 188 C.

Reference： [1]Patent: US4299834,1981,A

54
[ 1122-58-3 ]
[ 623564-42-1 ]
para-nitrobenzyl (5R,6S)-6-bromopenem-3-carboxylate [ No CAS ]
[ 623906-31-0 ]

Yield	Reaction Conditions	Operation in experiment
	With MgBr2; acetic anhydride; triethylamine; citric acid; In tetrahydrofuran; acetonitrile;	Step 6: 5R),(6Z)-6-(5,6-Dihydro-8H-imidazo[2,1-c][1,4]oxazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, sodium salt The dry acetonitrile (66 mL) solution of 5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazine-2-carbaldehyde (1.2 g) was added to the dry acetonitrile (66 mL) solution of MgBr2 (3.6 g) under a nitrogen atmosphere at room temperature then the mixture was stirred for 10 min. The dry THF (132 mL) solution of p-nitrobenzyl (5R,6S)-6-bromopenem-3-carboxylate (3.4 g) was added and the mixture was cooled to -20 C. then triethylamine (2.8 mL) was added in one portion. The reaction vessel was covered with foil to exclude light. The reaction mixture was stirred for 4 h at -20 C. and treated with 4-dimethylamino pyridine (100 mg) and acetic anhydride (1.5 mL) in one portion. The reaction mixture was warmed to 0 C. and stirred for 18 h at 0 C. 10% Citric acid aqueous solution (1 L) was added to the reaction mixture and the aqueous layer was extracted with ethyl acetate (3*500 mL). The combined organic layer was washed with water, saturated sodium hydrogen carbonate and brine, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and crude (5R)-6-[acetoxy-(5,6-dihydro-8H-imidazo[2,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester was obtained as brown amorphous solid.

Reference： [1]Patent: US2004/132708,2004,A1

55
[ 1122-58-3 ]
[ 7783-99-5 ]
[ 14172-90-8 ]
(4-N,N-dimethylaminopyridyl)(nitro)cobalt(III) tetraphenylporphyrin [ No CAS ]

Reference： [1]Inorganic Chemistry,2001,vol. 40,p. 4217 - 4225

56
[ 1122-58-3 ]
[ 131086-21-0 ]
C₇H₁₁N₂O₃⁽³²⁾P [ No CAS ]
[ 1145718-81-5 ]
C₈H₁₃N₃O₉⁽³²⁾P₂S [ No CAS ]
[ 1145718-73-5 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 303 - 307

57
[ 1122-58-3 ]
[ 3056-17-5 ]
C₇H₁₁N₂O₃⁽³²⁾P [ No CAS ]
[ 1145718-79-1 ]
C₁₀H₁₄N₂O₁₀⁽³²⁾P₂ [ No CAS ]
[ 1145718-72-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 303 - 307

58
[ 1122-58-3 ]
[ 57090-45-6 ]
[ 942209-57-6 ]

Reference： [1]Synthesis,2009,p. 1437 - 1444

59
[ 1122-58-3 ]
[ 60827-45-4 ]
[ 942209-56-5 ]

Reference： [1]Synthesis,2009,p. 1437 - 1444

60
[ 102-09-0 ]
[ 1122-58-3 ]
[ 33263-43-3 ]
[ 1225035-39-1 ]
[ 1225035-47-1 ]

Reference： [1]Molecules,2010,vol. 15,p. 1113 - 1126

61
[ 1943-83-5 ]
[ 1122-58-3 ]
[ 150683-30-0 ]
[ 1094837-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Example 28 {7-Chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}(2-chloroethyl)carbamate <strong>[150683-30-0]Tolvaptan</strong> (1.0 g, 2.2 mmol) was suspended in toluene (7 ml). 2-Chloroethyl isocyanate (0.28 ml, 3.3 mmol) and 4-dimethylaminopyridine (DMAP) (27 mg, 0.22 mmol) were added thereto, and the mixture was stirred at 80 C. for 24 hours. After cooling to room temperature, the insoluble materials were filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (n-hexane:ethyl acetate=54:46?33:67). The purified product was concentrated under reduced pressure to obtain 1.0 g of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}(2-chloroethyl)carbamate as white amorphous solid. 1H-NMR (DMSO-d6, 100 C.) delta ppm: 1.6-2.2 (4H, m), 2.36 (6H, s), 2.6-4.3 (2H, m), 3.42 (2H, t, J=6.0 Hz), 3.64 (2H, dd, J=6.0, 12.1 Hz), 5.8-5.9 (3H, m), 6.7-7.5 (10H, m), 7.56 (1H, s), 9.8 (1H, br).

Reference： [1]Patent: US2011/71084,2011,A1

62
[ 1122-58-3 ]
N₁-((ethylimino)methylene)-N₃,N₃-dimethylpropane-1,3-diamine hydrochloride (WSC) [ No CAS ]
[ 153910-62-4 ]
[ 150683-30-0 ]
[ 1094837-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; water;	Example 20 7-Chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 3-[2-(bis-benzyloxy-phosphoryloxy)-4,6-dimethyl-phenyl]-3-methyl-butyrate <strong>[150683-30-0]Tolvaptan</strong> (0.63 g), 3-[2-(bis-benzyloxy-phosphoryloxy)-4,6-dimethyl-phenyl]-3-methyl-butyric acid (0.70 g), and 4-dimethylaminopyridine (DMAP) (24 mg, 0.22 mmol) were suspended in dichloromethane (10 ml). N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (WSC) (383 mg) was added thereto, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was purified by silica gel flash chromatography (n-hexane:ethyl acetate=70:30?35:65). The purified product was concentrated under reduced pressure to obtain 0.92 g of 7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 3-[2-(bis-benzyloxy-phosphoryloxy)-4,6-dimethyl-phenyl]-3-methyl-butyrate as white amorphous solid. 1H-NMR (DMSO-d6, 100 C.) delta ppm: 1.5-1.9 (7H, m), 2.10 (3H, s), 2.32 (3H, s), 2.36 (3H, s), 2.6-4.3 (2H, m), 2.91 (2H, d, J=15.3 Hz), 3.13 (2H, d, J=15.3 Hz), 5.11 (2H, s), 5.14 (2H, s), 5.7-5.9 (1H, m), 6.74 (1H, s), 6.75-7.4 (20H, m), 7.54 (1H, s), 9.8 (1H, br).

Reference： [1]Patent: US2011/71084,2011,A1

63
[ 1122-58-3 ]
[ 33263-43-3 ]
[ 1335122-15-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	In acetonitrile; for 18h;Reflux;	General procedure: A mixture of the appropriate pyridine derivative (24 mmol) and 4-chloro-3-pyridienesulfonamide 1 (2.31 g, 12 mmol) in acetonitrile (15 ml) was refluxed with stirring for 18 h and left to stand at room temperature overnight. The precipitate was filtered off, washed with acetonitrile (5 .x. 2 ml) and dried. In this manner the following aminium chlorides were obtained.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4403 - 4410

64
[ 1122-58-3 ]
[ 33263-43-3 ]
[ 1335122-19-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4403 - 4410

65
[ 1122-58-3 ]
[ 39028-27-8 ]
[ 16806-35-2 ]
[ 1178574-43-0 ]

Reference： [1]Journal of the American Society for Mass Spectrometry,2011,vol. 22,p. 13 - 30

66
[ 1122-58-3 ]
[ 39028-27-8 ]
[ 5051-06-9 ]
[ 1178574-41-8 ]

Reference： [1]Journal of the American Society for Mass Spectrometry,2011,vol. 22,p. 13 - 30

67
[ 1122-58-3 ]
[ 1383732-69-1 ]
[ 961-38-6 ]
[(C₄H₂N(P(C₆H₅)2N(C₆H₄CH(CH₃)2))2)Lu(CH₂Si(CH₃)3)(NH(C₆H₂(C(CH₃)3)3))(C₅H₄N(N(CH₃)2))] [ No CAS ]

Reference： [1]Dalton Transactions,2012,vol. 41,p. 7873 - 7875

68
[ 1122-58-3 ]
[ 67-20-9 ]
[ 1443274-88-1 ]

Reference： [1]CrystEngComm,2013,vol. 15,p. 878 - 889

69
[ 1122-58-3 ]
[ 4836-69-5 ]
[ 1345477-57-7 ]
[ 25952-53-8 ]
[ 1345477-81-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	In dichloromethane; ethyl acetate; toluene;	9.1 Preparation of 2-(2,4-dinitrophenyl)ethyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]-ethyl}phenyl)prop-2-enoate 2.50 g (11.8 mmol) of <strong>[4836-69-5]2-(2,4-dinitrophenyl)ethanol</strong>, 4.91 g (11.8 mmol) of (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}phenyl)prop-2-enoic acid, 144 mg (1.2 mmol) of 4-di-methylaminopyridine are dissolved in 30 mL of dichloromethane. 2.48 g (13.0 mmol) of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC hydrochloride) are added at 0 C. The solution is stirred for 1 h at 0 C. and allowed to stir at room temperature overnight. After 22 hours at room temperature, the reaction mixture is partitioned between dichloro-methane and water. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Chromatography of the residue on 200 g silica gel using toluene: ethyl acetate 95:5 as eluent and crystallization from ethyl acetate:hexane mixture yields 5.11 g (71%) of 2-(2,4-dinitrophenyl)ethyl (2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenoxy]methyl}phenyl)prop-2-enoate as yellow crystals.

Reference： [1]Patent: US2013/35446,2013,A1 .Location in patent: Page/Page column

70
[ 1122-58-3 ]
[ 4479-74-7 ]
cis-[Ru(dmso)₄Cl₂] [ No CAS ]
[ 1445769-11-8 ]

Reference： [1]Inorganic Chemistry,2013,vol. 52,p. 7844 - 7852

71
[ 1122-58-3 ]
[ 1892-57-5 ]
[ 94-09-7 ]
[ 192762-72-4 ]
[ 1442439-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	Step 1 To a stirred mixture of 8-bromo-2,2-dimethyl-4-(p-tolyl)chromene-6-carboxylic acid (56 mg, 0.15 mmol) in dichloromethane (4 mL) was added 4-(dimethylamino)-pyridine (44 mg, 0.36 mmol) and ethyl-4-aminobenzoate (37 mg, 0.225 mmol). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (43 mg, 0.225 mmol) was then added and the reaction mixture was stirred at room temperature for 24 hours. The resulting solution was directly submitted to column chromatography on silica gel using dichloromethane as the mobile phase. Ethyl 4-[[8-bromo-2,2-dimethyl-4-(p-tolyl)chromene-6-carbonyl]amino]benzoate (69 mg, 0.133 mmol) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) ? 8.03 (2H, d, J=8.7 Hz), 7.91 (1H, d, J=2.1 Hz), 7.70 (1H, bs), 7.65 (2H, d, J=8.7 Hz), 7.50 (1H, d, 2.1 Hz), 7.25 (4H, s), 5.70 (1H, 1s), 4.359 (2H, q, J=7.1 Hz), 2.39 (3H, s), 1.56 (6H, s), 1.39 (3H, t, J=7.1 Hz).

Reference： [1]Patent: US2014/94512,2014,A1 .Location in patent: Page/Page column

72
[ 1122-58-3 ]
[ 13734-38-8 ]
(S)-(2-(7-Acetyl-4-(methoxymethyl)-3-methylbenzo[b]thiophene-2-carboxamido)quinolin-5-yl)methyl-3-(tert-butoxy)-2-((tert-butoxycarbonyl)amino)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;	Reference Example 146 (S)-(2-(7-Acetyl-4-(methoxymethyl)-3-methylbenzo[b]thiophene-2-carboxamido)quinolin-5-yl)methyl-3-(tert-butoxy)-2-((tert-butoxycarbonyl)amino)propanoate To a solution of the compound (220 mg) obtained in Example 79, <strong>[13734-38-8]N-(tert-butoxycarbonyl)-O-tert-butyl-L-serine</strong> (159 mg), and N,N-dimethyl-4-aminopyridine (136 mg) in DMF (5 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (116 mg) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate and saturated aqueous sodium chloride in this order. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25-20:80) to obtain the title compound (273 mg). 1H NMR (CDCl3, 400 MHz): delta (ppm) 8.71 (s, 1H), 8.58 (d, J=9.3 Hz, 1H), 8.44 (d, J=9.3 Hz, 1H), 8.10 (d, J=7.8 Hz, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.62-7.67 (m, 2H), 7.52-7.55 (m, 1H), 5.65-5.70 (m, 1H), 5.52-5.57 (m, 1H), 5.35-5.39 (m, 1H), 5.01 (s, 2H), 4.40-4.47 (m, 1H), 3.73-3.77 (m, 1H), 3.50-3.56 (m, 1H), 3.53 (s, 3H), 3.01 (s, 3H), 2.79 (s, 3H), 1.44 (s, 9H), 0.95-1.05 (s, 9H)

Reference： [1]Patent: US2016/24060,2016,A1

73
[ 1122-58-3 ]
[ 13710-19-5 ]
C₇H₁₀N₂*C₁₄H₁₂ClNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃;	General procedure: The equimolar ratio of API and the salt former were taken together in a 25 mL glass beaker, dissolved in a particular solvent of 10 mL (MFA-4AP: ethanol, MFA-DMAP: ethanol, TFA-4AP: methanol,TFA-DMAP: ethanol, NPX-4AP: methanol, NPX-2AP: ethanol) at 60 C and left for slow evaporation at room temperature. Good quality crystals suitable for SCXRD analysis were obtained in all thesix cases.

Reference： [1]Journal of Molecular Structure,2017,vol. 1141,p. 64 - 74

74
[ 1122-58-3 ]
[ 51436-99-8 ]
2,6-bis(3-fluoro-4-methylphenyl)-N,N-dimethylpyridin-4-amine [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 1970 - 1973

75
[ 1122-58-3 ]
[ 3744-87-4 ]
[ 1892-57-5 ]
[ 107-11-9 ]
(R)-tert-butyl (1-(allylamino)-1-oxopropan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With calcium sulfate;	Example 22 Preparation of (R)-tert-butyl (1-(allylamino)-1-oxopropan-2-yl)carbamate (C68) (R)-2-((tert-Butoxycarbonyl)amino)propanoic acid (5.26 g, 27.8 mmol) in dichloromethane (40 mL) in a round-bottomed flask was placed in a room temperature water bath. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.91 g, 30.3 mmol) was added followed by allyl amine (4.00 mL, 53.5 mmol) in 0.5 mL portions. 4-Dimethylaminopyridine (3.70 g, 30.3 mmol) was added, and the reaction mixture was stirred for 18 hours at room temperature while under a drying tube charged with calcium sulfate. The reaction mixture was washed with hydrochloric acid (10%, 3*). The organic layer was diluted with a dichloromethane (100 mL) and ethyl acetate (250 mL), washed with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated providing the title compound as a white solid (3.51 g, 55%): [a]3+30.60 (c 0.00620, dichloromethane); mp 87-94 C.; 1H NMR (400 MHz, CDCl3) delta 6.40 (s, 1H), 5.91-5.75 (m, 1H), 5.25-5.09 (m, 2H), 5.07 (s, 1H), 4.19 (d, J=10.6 Hz, 1H), 3.88 (t, J=5.8 Hz, 2H), 1.44 (s, 9H), 1.37 (d, J=7.1 Hz, 3H); EIMS m/z 228 ([M]+).

Reference： [1]Patent: US2017/208803,2017,A1

76
[ 1122-58-3 ]
[ 27372-38-9 ]
[ 89532-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; dichloromethane; at 20℃; for 24.0h;	The product of step 2 (10 mmol, 1.42 g) was dissolved in CH2Cl2,Add a certain amount of condensation agent 4 - dimethylaminopyridine and EDC, until the solid completely dissolved after adding ethanol. Room temperature reaction 24h, after the end of the reaction decompression pumping,Silica gel column chromatography to obtain a white powder.

Reference： [1]Patent: CN105017197,2017,B .Location in patent: Paragraph 0179; 0184; 0187

77
[ 1122-58-3 ]
[ 17890-56-1 ]
C₁₆H₁₇N₂S⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4388 - 4390

78
[ 1122-58-3 ]
C₂₆H₈F₁₀O₂Zn^(1-)*C₂₀H₃₀Fe⁽¹⁺⁾ [ No CAS ]
[ 12126-50-0 ]
2C₇H₁₀N₂*2C₆F₅^(1-)*Zn⁽²⁺⁾ [ No CAS ]
[ 84-11-7 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 3980 - 3983

79
[ 1122-58-3 ]
C₂₈H₈F₁₀O₂Zn^(1-)*C₂₀H₃₀Fe⁽¹⁺⁾ [ No CAS ]
[ 12126-50-0 ]
2C₇H₁₀N₂*2C₆F₅^(1-)*Zn⁽²⁺⁾ [ No CAS ]
[ 6217-22-7 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 3980 - 3983

80
[ 1122-58-3 ]
[ 1072-91-9 ]
[ 109-72-8 ]
[ 7397-46-8 ]
1-(diethylborylmethyl)-3,5-dimethylpyrazole·LiOMe(DMAP)₂ [ No CAS ]

Reference： [1]Organometallics,2018,vol. 37,p. 127 - 135

81
[ 1122-58-3 ]
[ 201230-82-2 ]
[ 461-81-4 ]
C₁₅H₁₄F₃N₂O₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 5350 - 5354

82
[ 1122-58-3 ]
1'-(2-hydroxyethyl)-3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-8-ol [ No CAS ]
[ 63521-92-6 ]
3',3'-dimethyl-6-nitro-1'-(2-(pent-4-enoyloxy)ethyl)spiro[chromene-2,2'-indolin]-8-yl pent-4-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In dichloromethane;	3',3'-dimethyl-6-nitro-1'-(2-(pent-4-enoyloxy)ethyl)spiro[chromene-2,2'-indolin]-8-yl pent-4-enoateor spiropyran was synthesized according to [15] with the following modifications made tothe amounts of reagents and purification methods. To an oven dried round bottom flask,1'-(2-hydroxyethyl)-3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indolin]-8-ol (3.0 g, 8.14 mmol, 1 equiv)and 4-dimethylaminopyridine (0.099 g, 0.814 mmol, 0.1 equiv.) were dissolved in dry dichloromethane(40 mL). The dark green suspension was stirred and <strong>[63521-92-6]4-pentenoic anhydride</strong> (3.20 mL, 17.51 mmol,2.15 equiv) was added in 3 separate aliquots, with 15 min between each addition. The reaction wasstirred overnight, resulting in a magenta-purple solution. The mixture was extracted with concentratedsodium bicarbonate solution (1 x 75 mL), 1 N hydrochloric acid (1 x 75 mL), water (2 x 75 mL)and brine (1x 75 mL) before drying over sodium sulfate. The crude product was collected fromrotary evaporation as crude purple oil. Boiling petroleum ether (300 mL) was poured into the oil,then the solution was hot filtered and let stand to develop yellow-green crystalline SP (3.21 g, 74%).Characterization matched the compound reported in literature [15].

Reference： [1]Molecules,2019,vol. 24

83
[ 67-56-1 ]
[ 1122-61-8 ]
[ 1122-58-3 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 15389 - 15398

84
[ 1122-58-3 ]
[ 632-58-6 ]
C₇H₁₀N₂*C₈H₂Cl₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.15%	In methanol; for 432.0h;	4-dimethylaminopyridine (12.2 mg, 0.10 mmol) was dissolvedin 3mL methanol. To this solution was added <strong>[632-58-6]tetrachlorophthalic acid</strong> (30.3 mg, 0.1 mmol) in 10 mL methanol. Colorless block crystals of 35 mg were afforded after 18 days by slow evaporation of the solvent (yield: 82.15%). mp 90e92 C. Elemental analysis: Calc. forC15H12Cl4N2O4 (426.07): C, 42.25; H, 2.82; N, 6.57. Found: C, 42.17;H, 2.71; N, 6.44. Infrared spectrum (KBr disc, cm1): 3728s (br,n(OH)), 3367s (multiple, nas (NH)), 3282s (ns (NH)), 3186w, 3159m,3098 m, 2980 m, 2877m, 1714s (ns (C]O)), 1610s (nas (CO2)),1555 m, 1513 m, 1472w, 1426 m, 1388s (ns (CO2)), 1350 m, 1306 m,1266s (ns (CeO)), 1225 m, 1182 m, 1139 m, 1095 m, 1053 m, 1013 m,966m, 922 m, 878 m, 833 m, 791m, 748 m, 705m, 661 m, 622 m,609 m.

Reference： [1]Journal of Molecular Structure,2020,vol. 1202

85
[ 1122-58-3 ]
[ 24424-99-5 ]
[ 1187449-01-9 ]
tert-butyl (4-bromo-5-chloropyridin-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	A. tert-butyl (4-bromo-5-chloropyridin-2-yl)carbamate, cpd 148a A solution of <strong>[1187449-01-9]4-bromo-5-chloropyridin-2-amine</strong> (2 g, 9.64 mmol), di-tert-butyldicarbonate (4.21 g, 19.28 mmol), TEA (2.93 g, 28.92 mmol), N,N-dimethylpyridin-4-amine (117.8 mg, 0.96 mmol) in CH2Cl2 (20 mL) was stirred at rt for 2 h. The mixture was diluted with water (40 mL) and extracted with CH2Cl2 (40 mL*3). The combined organic layers were dried (MgSO4), filtered, and the filtrate concentrated to give the crude product as a white solid. The crude product was purified by FCC (petroleum ether/ethyl acetate=100:0 to 70:30). The solvents were evaporated to afford the title compound as a white solid (1.2 g).

Reference： [1]Patent: US2019/381019,2019,A1

86
[ 1122-58-3 ]
[ 83-40-9 ]
C₇H₁₀N₂*2C₈H₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.04%	In methanol; ethanol;	4-dimethylaminopyridine (12.2 mg, 0.10 mmol) was dissolvedin 3mL methanol. To this solutionwas added <strong>[83-40-9]3-methylsalicylic acid</strong>(15.1 mg, 0.10 mmol) in 8mL ethanol. Colorless block crystals were obtained after a week by slow evaporation of the solvent (yield:32 mg, 75.04%, based on DMAP). mp 134e135 C. Elemental analysis:Calc. for C23H26N2O6 (426.46): C, 64.72; H, 6.10; N, 6.56. Found:C, 64.60; H, 6.02; N, 6.46. Infrared spectrum (KBr disc, cm1):3548w(n(HO)), 3358s(nas(NH)), 3246s(ns(NH)), 3145 m, 3084 m,2965 m, 2874m, 1682s(C]O), 1618s(nas(CO2)), 1560 m, 1517 m,1475 m, 1432 m, 1394s(ns(CO2)), 1350 m, 1307 m, 1265s(n(CeO)),1222 m, 1180 m, 1136 m, 1094 m, 1054 m, 1012 m, 870 m, 825 m,782 m, 742m, 696 m, 652 m, 610m.

Reference： [1]Journal of Molecular Structure,2020,vol. 1203

87
[ 1122-58-3 ]
[ 4224-69-5 ]
C₁₂H₁₇N₂O₂⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In tetrahydrofuran; at 20℃; for 2h;	4-(dimethylamino) pyridine (24.4 mg, 0.2 mmol) was dissolved in 100 pL of dry THF. To the solution, compound lb (50 mg, 0.28 mmol) was added. The reaction was kept for 2 hours at room temperature. Then the white precipitate was washed with diethyl ether for three times. The precipitate was collected and dried to achieve compound 5. Yield: 53.2 mg, 89%. ' H-N R (400 MHz, MeOH-d4): d 8.16 (d, J=7.79 Hz, 2H), 6.99 (d, J=7.79 Hz, 2H), 6.52(s, 1H), 6.08(s, 1H), 5.02(s, 2H), 3.76(s, 3H), 3.26 (s, 6H). l3C-NMR (100 MHz, MeOH-d4): 5(ppm) 166.53, 158.10, 143.43, 136.17, 132.28, 108.76, 58.93, 52.87, 40.36. MS (m/z): [M]+ calcd. for Ci2Hi7BrN02, 300.05; found, 221.3 for [M-Br]+.

Reference： [1]Patent: WO2020/6340,2020,A1 .Location in patent: Paragraph 00223

88
[ 1122-58-3 ]
[ 24424-99-5 ]
[ 10597-52-1 ]
[ 208772-95-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	(Step 1) tert-Butyl <strong>[10597-52-1]4-nitro-1H-benzimidazole</strong>-1-carboxylate To a suspension of <strong>[10597-52-1]4-nitro-1H-benzimidazole</strong> (2.65 g) in tetrahydrofuran (80.0 mL), triethylamine (3.38 mL) and di-tert-butyl dicarbonate (4.25 g) were added, and the mixture was stirred at room temperature for 1 hour. 4-Dimethylaminopyridine (0.0397 g) was then added to the mixture, and the resultant mixture was stirred at room temperature overnight. After the reaction solution was concentrated under reduced pressure, the residue obtained was purified by silica gel column chromatography (chloroform/ethyl acetate). After concentration under reduced pressure, diethyl ether was added to the solid obtained to obtain a suspension, and the suspension was filtered off and dried to obtain the title compound (3.94 g) as a solid. 1H-NMR (CDCl3) delta: 1.73 (9H, s), 7.53 (1H, t, J = 8.2 Hz), 8.20-8.22 (1H, m), 8.39-8.41 (1H, m), 8.62 (1H, s). MS (m/z) :164 (M-CO2tBu+H)+.

Reference： [1]Patent: EP3643703,2020,A1

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