[ CAS No. 6346-09-4 ] {[proInfo.proName]}

Name: 6346-09-4|4,4-Diethoxybutan-1-amine|97%
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Quality Control of [ 6346-09-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 6346-09-4 ]

CAS No. :	6346-09-4	MDL No. :	MFCD00008227
Formula :	C₈H₁₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GFLPSABXBDCMCN-UHFFFAOYSA-N
M.W :	161.24	Pubchem ID :	80672
Synonyms :

Calculated chemistry of [ 6346-09-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.45
TPSA :	44.48 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) :	-6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.4
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	1.12
Log Po/w (MLOGP) :	0.82
Log Po/w (SILICOS-IT) :	0.98
Consensus Log Po/w :	1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.76
Solubility :	28.3 mg/ml ; 0.176 mol/l
Class :	Very soluble
Log S (Ali) :	-1.11
Solubility :	12.6 mg/ml ; 0.078 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.84
Solubility :	2.34 mg/ml ; 0.0145 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.2

Safety of [ 6346-09-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P210-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405	UN#:	2735
Hazard Statements:	H314-H227	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 6346-09-4 ]

* 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 [ 6346-09-4 ]
Downstream synthetic route of [ 6346-09-4 ]

[ 6346-09-4 ] Synthesis Path-Upstream 1~5

1
[ 50-00-0 ]
[ 6346-09-4 ]
[ 1116-77-4 ]

Reference： [1] Tetrahedron Letters, 1994, vol. 35, # 15, p. 2401 - 2404

2
[ 6346-09-4 ]
[ 1116-77-4 ]

Reference： [1] Croatica Chemica Acta, 1964, vol. 36, p. 103,106

3
[ 6346-09-4 ]
[ 62-53-3 ]
[ 125541-22-2 ]

Reference： [1] Journal of Organic Chemistry, 1990, vol. 55, # 8, p. 2552 - 2554

4
[ 6346-09-4 ]
[ 637-60-5 ]
[ 1010-95-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	With zinc(II) chloride In toluene at 100℃; for 1 h;	In a 250 mL glass bottle, p-tolylhydrazine hydrochloride (5.0 g, 31.5 mmol), ZnCl₂ (6.19 g, 38 mmol, 1.2 eq) and 4,4-diethoxybutan-1-amine (8.6 g, 62.9 mmol, 2 eq) were suspended in toluene (80 mL) and allowed to stir at 100 °C for 1 h. After completion, the reaction mixture was allowed to cool at RT and then made alkaline with aqueous NaOH (1N, 250 mL). The mixture was extracted with EtOAc (3 × 300 mL). The combined organic layers were dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure. The residue was purified by SiO₂ chromatography (0-8percent MeOH in CH₂Cl₂) to obtain 2-(5-methyl-1H-indol-3-yl)ethanamine which was treated with excess ethanolic HCl and allowed to stir for 10 min. The volatiles were then removed under reduced pressure. The residue obtained was stirred in Et₂O and filtered to obtain 2-(5-methyl-1H-indol-3-yl)ethanamine hydrochloride (3.8 g, 57percent).¹H NMR: (400 MHz, CDCl₃) δ 8.06 (br s, 1H), 7.40 (s, 1H), 7.24 (d, 1H), 7.05 (d, 1H), 7.00 (s, 1H), 3.01 (t, 2H), 2.88 (t, 2H), 2.44 (s, 3H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 20, p. 5103 - 5109

5
[ 6346-09-4 ]
[ 139272-29-0 ]
[ 88919-22-6 ]

Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 4, p. 590 - 594

[ 6346-09-4 ] Synthesis Path-Downstream 1~59

1
[ 6139-83-9 ]
[ 6346-09-4 ]
[ 109498-52-4 ]

Reference： [1]Chemicke Zvesti,1959,vol. 13,p. 163,166
Chem.Abstr.,1959,p. 20107

2
[ 870-72-4 ]
[ 6346-09-4 ]
[ 151-50-8 ]
[ 1006878-78-9 ]

Reference： [1]Journal of the Chemical Society,1951,p. 239,242

3
[ 6346-09-4 ]
[ 98-09-9 ]
2-ethoxy-1-(phenylsulfonyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: To a cooled solution (5-8) of 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) and triethylamine (3.5ml) in dichloromethane (100 ml) sulfonyl chloride (20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 2.
95%		General procedure: The appropriate sulfonyl chloride (20 mmol) wasadded with cooling (5-8) to a solution of 4,4-diethoxybutan-1-amine (3.4 g, 20 mmol) and Et3N (3.5 ml) inCH2Cl2 (100 ml). The reaction mixture was stirred at roomtemperature for 12 h. The reaction mixture was thenwashed with saturated aqueous NaHCO3 solution (100 ml),the organic layer was separated, and the solvent wasremoved under reduced pressure. 2-Ethoxy-1-tosylpyrrolidine (5a). Yield 2.21 g (58%),beige powder, mp 85-86. IR spectrum, nu, cm-1: 1161(SO2), 1596 ( Ar). 1H NMR spectrum (CDCl3), delta, ppm(J, Hz): 1.20 (3H, t, J = 7.0, CH3); 1.35-1.52 (1, m), 1.69-1.80 (1, m), 1.82-1.92 (1, m), and 1.95-2.09 (1, m,2CH2); 2.44 (3, s, 3); 3.09-3.20 (1, m), 3.37-3.44(1, m), 3.54-3.60 (1, m), and 3.78-3.84 (1, m, 2CH2);5.20-5.25 (1, m, ); 7.32 (2, d, J = 8.1, Ar); 7.74(2, d, J = 8.2, Ar). 13C NMR spectrum (CDCl3), delta, ppm:15.0; 21.5; 23.2; 32.9; 47.2; 63.1; 90.2; 127.4; 129.6;136.1; 143.3. Found, %: 58.09; H 7.23; N 5.07; S 11.81.C13H19NO3S. Calculated, %: 57.97; H 7.11; N 5.20;S 11.90.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 44 - 52
[2]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 161 - 166
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 161 - 166,6
[3]Chemische Berichte,1905,vol. 38,p. 4159

4
[ 50-00-0 ]
[ 6346-09-4 ]
[ 1116-77-4 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 2401 - 2404

5
[ 6346-09-4 ]
[ 24424-99-5 ]
[ 143646-48-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3.5h;	To a solution of commercially available 4-aminobutyaldehyde diethyl acetal (21)[1] (5.00 g, 31.0 mmol) in THF (75 mL) was added TEA (6.50 mL, 4.70 g, 46.5 mmol) at 0-5 C (ice-bath temperature). The mixture was allowed to stir for 5 min, and treated with a solution of Boc2O (6.76 g, 31.0 mmol) in THF (30 mL) drop-wise. The reaction mixture was stirred at 0-5 C for 30 min and allowed to warm to RT.and stir for 3 h. The mixture was transferred to a separatory funnel and partitioned with H2O (100 mL) and EtOAc (200 mL). The organic layer was separated, dried (anhydrous Na2SO4), filtered and concentrated to afford 7.71 g (95% yield) of compound 22 as a viscous slightly yellow oil: 1H NMR (400 MHz,CDCl3) delta 4.63 (bs, 1H), 4.46 (t, J = 5.39 Hz, 1H), 3.55 (ABq of q, J = 9.32, 7.14 Hz, Dn = 62.10 Hz, 4H), 3.12 (q, J = 6.40 Hz, 2H), 1.65 - 1.60 (m, 2H), 1.57 - 1.50 (m, 2H), 1.42 (s, 9H), 1.18 (t, J = 6.90 Hz, 3H). 13C NMR (100 MHz, DMSO-d6) delta 156.10, 102.47, 77.83, 60.99, (BocNHCH2- obscured by DMSO solvent peak ), 31.18, 28.78, 25.36, 15.83. HRMS ESI-TOF (m/z) = 284.1814 (284.1832 calculated for C13H27NO4Na) [M+Na].
89%	With triethylamine; In dichloromethane; at 0℃;	In a flask were added 77 4,4-diethoxybutan-1-amine (2 g, 12.4 mmol), 31 triethylamine (1.8 mL, 12.9 mmol) and DCM (10 mL). The solution was cooled to 0 C. To this solution was added dropwised a solution of Boc2O (2.7 g, 12.4 mmol) in 68 DCM (10 mL). The solution was stirred overnight then evaporated. The compound was purified by flash chromatography by using 15 ethyl acetate/78 hexane (10/90) to (30/70) to give (0.72 g, 89%). 1H NMR (CDCl3) delta (ppm) 1.17 (t, 6H, CH3), 1.43 (s, 9H, CH3), 1.55 (m, 4H, CH2), 3.12 (d, 2H, CH2), 3.45 (m, 2H, CH2), 3.47 (m, 2H, CH2), 4.47 (t, 1H, CH), 4.64 (s, 1H, NH).

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 10035 - 10044
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1897 - 1902
[3]Patent: US9809621,2017,B2 .Location in patent: Page/Page column 37
[4]Journal of the Chemical Society. Perkin transactions I,1993,p. 2843 - 2850
[5]Tetrahedron Letters,1996,vol. 37,p. 3379 - 3382
[6]Journal of Organic Chemistry,1998,vol. 63,p. 2993 - 3005
[7]Journal of the American Chemical Society,2012,vol. 134,p. 16449 - 16451,3

6
[ 6346-09-4 ]
[ 22509-74-6 ]
[ 32464-55-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In tetrahydrofuran; at 20℃; for 16h;Cooling with ice;	Step1 To the stirred solution of 1,3-dioxo-1,3-dihydro-isoindole-2-carboxylic acid ethyl ester (10 g, 62 mmol, 1 eq) in dry THF (200 mL) were added 4,4-diethoxy-butylamine (13.6 g, 62 mmol, 1 eq) and TEA (8.6 mL, 62 mmol, 1 eq) under ice cooled condition and stirred at RT for 16 h. After completion of the reaction, it was concentrated under reduced pressure to obtain crude product which was purified by silica gel (100-200 mesh) column chromatography (5% EA/Hexane) to afford 2-(4,4-diethoxy-butyl)-isoindole-1,3-dione (17 g, 94% yield) as light yellowish liquid.
	In acetonitrile;	Synthesis of phthalimide lb.; To a stirred solution of 4-aminobutyraldehyde diethyl acetal la (89.3 mmol) in CH3CN (100 mL) was added N-carbethoxyphthalimide (93.8 mmol). Once the reaction was complete, the acetonitrile was removed under reduced pressure and the aqueous phase extracted with EtOAc (x3). The organic phase were combined, then washed with water (x4), saturated brine (x3), then dried (Na2S04), filtered, and evaporated under reduced pressure to give the title compound lb, which crystallized on standing.
	With triethylamine; In tetrahydrofuran; at 20℃;	To a solution of [4,4-bis(ethyloxy)butyl]amine (5.0 g, 30.0 mmol) and Et3N (4.61 ml, 33.0 mmol) in 40 ml_ of THF was added ethyl 1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindole-2- carboxylate (6.9 g, 32.0 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was extracted with hexane. The hexane solution was concentrated in vacuo and heated at 100 0C under reduced pressure to remove ethylcarbamate by sublimation. The mixed solution of diethyl acetal (2.0 g, 6.95 mmol) thus obtained and 1 Lambda/aq. HCI (14 ml_) in acetone (20 ml_) was heated under reflux for 15 min. Acetone was evaporated and aqueous layer was extracted with ether, dried over MgSO4, and filtered. The solvent was evaporated and the residue was moved to next step.

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20℃; for 2.25h;

Phthalimide Protection: (0158) Deionized water (50 mL) and THF (50 mL) were added in a 250-mL flask. NaHCO3 (5.67 g, 67.5 mmol) and 4-aminobutyraldehyde diethyl acetal (8) (12.0 mL, 67.5 mmol) were suspended in this solution. N-carbethoxyphthalimide (9) (15.54 g, 70.9 mmol) was then added and the solution began become clear within 15 minutes. The reaction was kept at ambient temperature for two hours and was diluted with EtOAc (500 mL) and water (20 mL) to dissolve the salt precipitation. The organic phase was separated and washed with brine (100 mL×2). It was then dried over Na2SO4, filtered, and concentrated to a colorless crude product. The residue was loaded on Biotage column (40 M x 2, 5-27% EtOAc in Hex in 16 CV) and a colorless product (10) was collected (95-100% yield). The product solidified after overnight high vacuo drying. Rf=0.43 (Hex:EtOAc=3:1), LC-MS (ESI, MH) 292.1. 1H NMR (300 MHz, CDCl3) delta 1.19 (6H, t, J=7.2 Hz), 1.65-1.80 (4H, m), 3.46-3.54 (2H, m), 3.58-3.74 (4H, m), 4.51 (1H, t, J=5.7 Hz), 7.70-7.74 (2H, m), 7.83-7.86 (2H, m).

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 526 - 531
[2]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721
[3]Patent: US2018/78541,2018,A1 .Location in patent: Paragraph 0394; 0396
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 946 - 979
[5]Journal of the American Chemical Society,2012,vol. 134,p. 16143 - 16146
[6]Organic and Biomolecular Chemistry,2014,vol. 12,p. 6094 - 6104
[7]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 1025 - 1030
[8]Tetrahedron Letters,1995,vol. 36,p. 4533 - 4536
[9]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 999 - 1002
[10]Tetrahedron,1991,vol. 47,p. 3305 - 3312
[11]Patent: WO2005/70930,2005,A2 .Location in patent: Page/Page column 36
[12]Patent: WO2007/30761,2007,A2 .Location in patent: Page/Page column 49; 145
[13]Patent: US2017/28077,2017,A1 .Location in patent: Paragraph 0158

7
[ 6346-09-4 ]
[ 62-53-3 ]
[ 125541-22-2 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 2552 - 2554

8
[ 6346-09-4 ]
[ 1234-35-1 ]
[(S)-1-(4,4-Diethoxy-butylcarbamoyl)-4-guanidino-butyl]-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 3755 - 3758

9
[ 6346-09-4 ]
[ 25341-42-8 ]
[(S)-2-Cyclohexyl-1-(4,4-diethoxy-butylcarbamoyl)-ethyl]-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 3755 - 3758

10
[ 6346-09-4 ]
[ 28697-11-2 ]
(S)-2-(4,4-Diethoxy-butylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 3755 - 3758

11
[ 50-00-0 ]
[ 6346-09-4 ]
[ 105-50-0 ]
[ 23692-06-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogenchloride; methyl orange; In ethanol; water; at 20℃; for 72h;	Compound 93 (100 g, 0.625 mol), 800 mL of ethanol and 0.15 g (0.45 mmol) of helianthin (methyl orange) were mixed. To the stirred mixture, 225 mL of a dilute hydrochloric acid (2.74 M) was slowly added followed by 45.8 ml (0.625 mol) of a formaldehyde solution, 124.8 g (0.625 mol) of compound 94 and 150 mL of ethanol were added. The mixture was stirred at room temperature for 3 days. The mixture was concentrated in vacuo to ca.500 mL. The mixture was cooled in an ice bath before the addition of IN NaOH (625 mL) which cause the separation of an oily solid. The aqueous phase was separated and the residue was triturated in ether (250 mL). After 30 min, the precipitate was collected by filtration, washed with ether (2x60 mL), and dried in vacuo to afford 95 as a pale yellow solid (1 10 g, 62%). LCMS:m z 284 (M+l)+.

Reference： [1]Patent: WO2013/43232,2013,A2 .Location in patent: Paragraph 00584
[2]Heterocycles,1996,vol. 43,p. 1391 - 1402

12
[ 6346-09-4 ]
[ 501-53-1 ]
[ 197891-66-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In diethyl ether; water; at 0 - 20℃;	[00295] To a solution of 4-aminobutanal diethyl acetal (Aldrich, St. Louis, MO) (1 g, 6.2 mmol) in 25 mL ether was added 25 mL water followed by potassium carbonate (2.6 g, 18.6 mmol) and the resulting colorless biphase cooled to 0 oC with vigorous stirring. To this was added benzyl chloroformate (0.88 mL, 6.2 mmol) dropwise over ten minutes and the resulting mixture allowed to slowly warm to rt overnight. The phases were separated and the aqueous extracted with ether. The organics were combined, washed twice with an aqueous 10% citric acid solution, then brine, dried (MgS04), filtered, and the filtrate cone, to a colorless oil. This was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give benzyl (4,4- diethoxybutyl)carbamate (1.56 g, 5.3 mmol, 85%) as a colorless oil. 1H NMR (300 MHz, CDC13) delta: ppm 7.32 (m, 5H); 5.09 (s, 2H); 4.88 (s, 1H); 4.48 (t, 2H, J = 5.3 Hz); 3.70-3.55 (m, 2H); 3.54-3.40 (m, 2H); 3.22 (quart.; 2H, J = 12.5 Hz, 6.2 Hz); 1.71-1.51 (m, 4H); 1.20 (t, 6H, J = 7.0 Hz).
	With sodium carbonate; In dichloromethane; water; at 0 - 20℃; for 3h;Inert atmosphere;	A solution of Na2CO3 (5.81g, 54.8mmol, 3.3equiv) in 50ml of water was added to a solution of 4-aminobutyraldehyde diethyl acetal (2.64g, 16.6mmol) in 50ml of CH2Cl2 and cooled to 0C. Benzyl chloroformate (3g, 17.6mmol, 2.5ml, 1.07equiv) was added dropwise and the reaction mixture was stirred at rt for 3h, after which the organic phase was separated and evaporated to dryness in vacuum. The residue 2038 was cooled to 0C and stirred with a solution of Sc(OTf)3 (81mg, 0.17mmol, 1mol%) in 166ml of heptane/EtOAc (70:30). After 45min, the reaction was warmed to rt and stirred for further 105min followed by removal of solvent in vacuum. The crude product on purification by CC (SiO2, Isohexane/EtOAc/EDMA=95:5:3) afforded 3.67g (90%) of (RS)-21 as colourless oil.

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 518 - 521
[2]Patent: WO2018/170306,2018,A1 .Location in patent: Paragraph 00295
[3]Journal of Medicinal Chemistry,1998,vol. 41,p. 3919 - 3922
[4]Synlett,1998,p. 1375 - 1377
[5]Tetrahedron Asymmetry,2005,vol. 16,p. 2521 - 2524
[6]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1284 - 1306

13
N'-(4,4-diethoxy-butyl)-N,N-dimethyl-formamidine [ No CAS ]
[ 6346-09-4 ]
[ 114094-45-0 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 991 - 997

14
[ 6346-09-4 ]
[ 5105-78-2 ]
[ 746677-09-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 20℃;

Reference： [1]Ropp, Sandrine; Guy, Julia; Berl, Valerie; Bischoff, Pierre; Lepoittevin, Jean-Pierre [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 13, p. 3619 - 3625]

15
[ 6346-09-4 ]
[ 130296-37-6 ]
4-[9-(1-hexylheptyl)-1,3,8,10-tetraoxo-3,8,9,10-tetrahydro-1H-anthra[2,1,9-def:6,5,10-d'e'f']diisoquinolin-2-yl]butyraldehyde [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 4328 - 4336

16
[ 6346-09-4 ]
[ 1116-77-4 ]

Reference： [1]Croatica Chemica Acta,1964,vol. 36,p. 103,106

17
[ 773-64-8 ]
[ 6346-09-4 ]
[ 639505-01-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; In chloroform; water; at 5℃; for 2h;	Amine 1 (Aldrich) (3. 5g, 21.7 mol) was dissolved in a mixture of chloroform (30 ml) and IN sodium hydroxide (24 ml) and [15ML] of mesitylenesulfonyl chloride dissolved in [1 SML] of chloroform were added at [5C.] The mixture was stirred for 2h, the reaction mixture was then diluted with chloroform (50 ml), the organic layer was separated, washed with a saturated solution of ammonium chloride, dried [(NA2S04),] and evaporated to dryness. The residual oil crystallized after drying and was used in the next step without further purification; 7. 0g (95%) of 2 were obtained [;'HNMR (CDC13)] : [PPM] 1.15 (t, 6H), 1.55 (m, 4H), 2.30 (s, 3H), 2.65 (s, 6H), 2.95 (q, 2H), 3.40-3. 55 [(M,] 4H), 4.40 (t, 1H), 4.90 (t, 1H), 6.95 (s, 2H) [; 13CNMR (CDCL3)] : [PPM] 15.19, 20.80, 22.85, 24.55, 30.83, 42.39, 61.40, 102.41, 131.84, 133.82, 138.99, 141.92.

Reference： [1]Patent: WO2004/2991,2004,A1 .Location in patent: Page 27

18
[ 6346-09-4 ]
[ 78-94-4 ]
[ 2407-99-0 ]

Yield	Reaction Conditions	Operation in experiment
24%		The compound was prepared according to J. Chem. Soc, Perkin Trans. 1 1986, 447-453, which is hereby incorporated by reference in its entirety. [00441] A mixture of but-3-en-2-one (5.4 g, 75 mmol) was added dropwise over ca. 10 minutes to a solution of 4,4-diethoxybutan-l -amine (9.6 g, 60 mmol) in Et20 (30 ml) at 0 C under nitrogen. The mixture was stirred at 0 C for a further 60 minutes then extracted with 2.5 M HC1 (150 ml). The aqueous acid layer was then heated to reflux and stirred for 150 minutes. After allowing to cool to room temperature, the mixture was concentrated in vacuo to about one third of the original volume. The mixture was cooled to 0 C and CH2C12 (200 ml) was added, followed by 3N NaOH until pH > 10. The aqueous and organic layers were partitioned and the organic layer was washed with a K2C03 solution (xl). The combined aqueous layers were extracted with CH2C12 (2 x 150 ml) and then the combined organic layers were dried (K2C03), filtered and concentrated in vacuo. The residue was dry-loaded on to silica gel and purified by column chromatography on silica gel using CH2C12 / MeOH (100:0 to 94:6 in increments of 2% MeOH) to give the desired product (2.0 g, 24%) as an oil. [00442] 1H NMR (300 MHz; CDC13) delta 3.37-3.30 (m, 1H), 3.20-3.14 (m, 1H), 2.68-2.51 (m, 2H), 2.40-2.19 (m, 5H), 2.03-1.93 (m, 2H), 1.91-1.80 (m, 1H), 1.60-1.48 (m, 1H). [00443] 13C NMR (75 MHz; CDC13) delta 209.3, 64.2, 53.3, 50.3, 47.4, 40.7, 31.5, 22.6
		According to the procedure described in J. Chem. Soc. Perkin Trans. I, 1986, 447-453, 3.6 ml of but-3-en-2-one are added dropwise under cold conditions to a mixture comprising 6 ml of 4,4-diethoxy-1-butamine in 20 ml of Et2O. The reaction medium is left stirring at AT for 1 h. The reaction medium is decanted into 50 ml of a 2.5M HCl solution and extracted with ether. The aqueous phase is left under warm conditions for 3 h. After cooling and evaporating to dryness, the crude product is taken up in H2O/K2CO3 and extracted with DCM, and the DCM extract is dried and concentrated.The expected product is obtained by vacuum distillation (40 C., 0.3 mmHg). 1.5 g of the expected product are obtained.
		Hexahydroindolizin-7(1H)-one (140): Prepared according to WO0000487A1, U.S. Pat. No. 5,874,427, WO0017198A1.

		To a solution of 4-aminobutyraldehyde diethyl acetal (2.51 mL, 14.3 mmol) in Et2O (5 mL) was added methyl vinyl ketone (1.21 mL, 14.3 mmol). After 1 h, concentrated HCl (5 mL) was added, and the reaction mixture was heated at 100 C. for 2 h. The mixture was concentrated to give hexahydroindolizin-7(1H)-one, which was carried forward without purification. The crude residue was diluted with EtOH (5 mL), and 3-bromophenylhydrazine hydrochloride (1.02 g, 4.47 mmol) was added followed by concentrated HCl (5 mL). The reaction mixture was heated at reflux overnight. After the mixture was concentrated, the residue was purified by flash column chromatography (silica gel, 5% CH3OH in CH2Cl2) to give the title compound (0.15 g, 12%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) delta 10.95 (s, 1H), 7.43-7.42 (d, J=1.6 Hz, 1H), 7.29-7.26 (d, J=8.3 Hz, 1H), 7.03-7.03 (dd, J=8.4, 1.8 Hz, 1H), 4.10-4.05 (d, J=13.4 Hz, 1H), 3.22-3.14 (m, 2H), 2.92-2.88 (d, J=13.7 Hz, 1H), 2.57-2.40 (m, 2H), 2.32-2.22 (m, 1H), 2.09-1.98 (m, 1H), 1.88-1.75 (m, 2H), 1.57-1.53 (m, 1H); ESI MS m/z 291 [M+H]+.
10.5 g		To a solution of 4,4-diethoxybutan-1 -amine (50.0 g) in diethyl ether (120 mL) stirredunder a nitrogen atmosphere at 000 was added but-3-en-2-one (21 .7 g) dropwise. After stirringfor 1 hour, aq. HCI solution (37%, 127 mL) was added dropwise. The reaction mixture was stirred at 100C for 2 hours. After cooling, the mixture was concentrated. Water was added. The pH was adjusted to 8-10 with sat. K2003 solution. The resulting mixture was extracted with DCM (2x100 mL). The combined organic layers were dried and concentrated. The residuewas distilled to afford hexahydroindolizin-7(1H)-one (10.5 g) as a colorless liquid.

Reference： [1]Patent: WO2013/152198,2013,A1 .Location in patent: Paragraph 00440; 00441; 00442; 00443
[2]Patent: US2010/35907,2010,A1 .Location in patent: Page/Page column 16
[3]Patent: US2006/258721,2006,A1 .Location in patent: Page/Page column 76; 77
[4]Patent: US2011/3738,2011,A1 .Location in patent: Page/Page column 32
[5]Patent: WO2015/181186,2015,A1 .Location in patent: Page/Page column 133

19
[ 6346-09-4 ]
[ 156866-52-3 ]
C₂₁H₃₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The compound (1.04 g) obtained in Example 23-3 was dissolved in anhydrous methanol (40 ml) and added with 4,4-diethoxy-butylamine (863 mg) and trimethyl orthoformate (1.44 ml). The whole was stirred at room temperature for 3 hours. The solution was added with sodium borohydride (499 mg) and the whole was stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off. The resultant was added with water, subjected to extraction with chloroform, and then dried with magnesium sulfate. The solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate). The resultant was dissolved in methanol (25 ml) and water (4.8 ml) and added with acrylonitrile (0.43 ml). The whole was stirred at room temperature for 16.5 hours. After completion of the reaction, the solvent was distilled off. The resultant was subjected to extraction with chloroform and dried with magnesium sulfate. The solvent was distilled off. The resultant was dissolved in THF (12 ml), acetone (12 ml), and 1 mol/l hydrochloric acid (12 ml) and the whole was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The resultant was dissolved in anhydrous methanol (26 ml) and added with piperidine (0.49 ml) and sodium cyanoborohydride (415 mg). After the solution was adjusted to pH 5 with acetic acid, the whole was stirred at room temperature for 3 days. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subj ected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.13 g) as a colorless oily substance. MS(FAB,Pos.):m/z=429[M+H]+ 1H-NMR(500MHz,CDCl3):delta=1.27-1.50(6H,m),1.47(9H,s),1.55-1.60(4H,m),2.25(2H,t,J=7.3Hz),2.34(4H,br),2.40(2H,t,J=7.0Hz),2.49(2H,t,J=6.9Hz),2.77(2H,t,J=7.0Hz),3.59(2H,s),4.31(2H,d,J=5.5Hz),7.23(2H,d,J=7.9Hz),7.29(2H,d,J=8.2Hz).

Reference： [1]Patent: EP1724263,2006,A1 .Location in patent: Page/Page column 85

20
[ 6346-09-4 ]
[ 24424-99-5 ]
[ 84766-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hydrogenchloride; hexanes - ether; chloroform;	EXAMPLE 5 N-t-BOC-2-pyrrolidinol (6) Di-t-butyl dicarbonate (2.3 ml; 10 mmol) was added dropwise to a solution of 4-aminobutyraldehyde diethyl acetal (1.73 ml; 10 mmol) in chloroform (20 ml). Warming of the solution and evolution of a gas were observed. After 10 minutes, TLC (silica gel, CH2 Cl2 --CH3 OH, 20:1) showed complete consumption of the starting amine and a single product spot, Rf=0.8. Solvent was removed, giving a colorless oil. The crude product was dissolved in a mixture of THF (30 ml) and hydrochloric acid (0.50 N, 30 ml). Stirring was continued for 2 hours. Then the mixture was diluted with brine (50 ml) and extracted with ether (325 ml). The combined ether portions were washed with water, saturated bicarbonate, and brine, and dried (MgSO4). After removal of solvent, the colorless oil was purified by chromatography on silica gel (Baker; 218 cm) in hexanes - ether (2:1), giving pure 6 (0.35 g, 1.87 mmol, 19%) as a colorless oil. TLC (silica gel, hexanes-ether, 2:1) Rf=0.5. MS m/e 170 (M+ -OH). NMR (CDCl3): delta1.48 (9H,S); 1.8-2.1 (4H,m); 3.2-3.7 (2H,m); 4.2-4.4 (1H, broad); 5.4-5.6 (1H, broad). IR (CHCl3): 3700-3400, 3000, 2920, 1675 cm-1.
	With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; chloroform;	EXAMPLE 52 Improved Procedure for: N-t-BOC-4-Aminobutyraldehyde carbobenzoxyhydrazone (7) A solution of 4-aminobutyraldehyde diethyl acetal (9.33 g) and di-t-butyldicarbonate (13.3 g) in chloroform (120 ml) was allowed to stir for 2 hrs. The mixture was concentrated and to the residue were added THF (110 ml) and hydrochloric acid (0.5 N; 120 ml). The mixture was stirred vigorously for 1 hr, then cooled in an ice-bath and diluted with ether (100 ml). Sodium hydroxide solution (1 N) was added until the aqueous layer was slightly basic (pH=8). The layers were separated and the aqueous layer extracted with ether (3*100 ml). The combined ether positions were washed with H2 O and brine, and dried (K2 CO3). Evaporation gave crude N-t-BOC-2-pyrrolidinol (6) as a colorless oil (20 g). This material was combined with carbobenzoyhydrazine (6.64 g) and THF (60 ml).

Reference： [1]Patent: US4634715,1987,A
[2]Patent: US4634715,1987,A

21
[ 6346-09-4 ]
[ 605-65-2 ]
[ 1110651-08-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine; In dichloromethane; at 25℃; for 1h;	N-(4,4-Diethoxybutyl)-5-(dimethylamino)naphthalene-l-sulfonamide (13). To a solution of dansyl chloride (270 mg, 1.00 mmol) in CH2C12 (10 mL) was added 4- aminobutyraldehyde diethyl acetal (237 L, 1.20 mmol) and Et3N (170 ih, 1.20 mmol). The solution was stirred for 1 h at 25 C and was then evaporated to dryness under reduced pressure. The material left was processed and purified under conditions identical to those described for the processing and purification of 11. Fractions containing the product were collected and evaporated to dryness under low pressure affording 13 (366 mg, 930 muetaiotaomicron) as a solid in a yield of 93 %. NMR (300 MHz, DMSO-c 6): delta 8.45 (dt, J = 8.5, 1.1 Hz, 1 H), 8.30 (dt, J= 8.8, 0.9 Hz, 1H), 8.09 (dd, J= 7.3, 1.2 Hz, 1 H), 7.89 (t, J= 5.5 Hz, 1H), 7.61 (t, J= 8.5 Hz, 1H), 7.58 (t, J= 8.5 Hz, 1H), 7.25 (dd, J= 7.6, 0.7 Hz, 1H), 4.19 (t, J= 5.3 Hz, 1H), 3.36 (m, 2H), 3.23 (m, 2H), 2.81 (s, 6H), 2.77 (t, J = 5.5 Hz, 2H), 1.31 (m, 4H), 0.99 (t, J= 7.0 Hz, 6H). I3C NMR (75 MHz, DMSO-< 6): 5 151.2, 136.1 , 129.2, 128.9, 128.1 , 127.7, 123.5, 1 19.1 , 1 14.9, 101.6, 60.2, 44.9, 42.2, 30.1 , 24.4, 15.1. +ESI-HRMS: Calcd for C2oH3oN204S [M + H]+ 395.1999, found 395.2000.

Reference： [1]Nucleic Acids Research,2012,vol. 40,p. 2312 - 2329
[2]Patent: WO2012/138530,2012,A1 .Location in patent: Page/Page column 41-42
[3]European Journal of Organic Chemistry,2008,p. 5383 - 5386

22
[ 6346-09-4 ]
[ 28920-43-6 ]
[ 1154759-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	N-Fmoc-4-amino-butyraldehyde diethyl acetal 4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.; Procedure 10: Protection of Amine by Fmoc Group To a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion- wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	To a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion-wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).; N-Fmoc-4-amino-butyraldehyde diethyl acetal4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	Protection of Amine by Fmoc Group: To a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion-wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).

	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	Procedure 10: Protection of Amine by Fmoc GroupTo a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion- wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).; N-Fmoc-4-amino-butyraldehyde diethyl acetal 4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h;	4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h;	Procedure 16: Protection of Amine by Fmoc GroupTo a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion-wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield). Example 43 6'-(4-Amino-butyl)-l-(4-amino-2(5)-hydroxy-butyryl)-sisomicinN-Fmoc-4-amino-butyraldehyde diethyl acetal4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 16 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	N-Fmoc-4-amino-butyraldehyde diethyl acetal 4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.; Procedure 10: Protection of Amine by Fmoc Group To a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion- wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	N-Fmoc-4-amino-butyraldehyde diethyl acetal4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 16 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification; Procedure 16: Protection of Amine by Fmoc GroupTo a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to O0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion-wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).

Reference： [1]Patent: WO2010/42850,2010,A1 .Location in patent: Page/Page column 52; 61-62
[2]Patent: WO2011/44501,2011,A2 .Location in patent: Page/Page column 59-60; 71
[3]Patent: WO2011/44498,2011,A1 .Location in patent: Page/Page column 65, 75-76
[4]Patent: WO2011/44503,2011,A1 .Location in patent: Page/Page column 73
[5]Patent: WO2011/44538,2011,A1 .Location in patent: Page/Page column 100
[6]Patent: WO2009/67692,2009,A1 .Location in patent: Page/Page column 45; 162
[7]Patent: WO2010/42851,2010,A1 .Location in patent: Page/Page column 52; 61-62
[8]Patent: WO2010/132777,2010,A2 .Location in patent: Page/Page column 169-170; 47

23
[ 6346-09-4 ]
[ 108-24-7 ]
[ 68029-07-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		Triethylamine (25.6 mL, 185 mmol, 2 eq.) at 0 C was added to a solution of 4-aminobutyraldehyde diethyl acetal (15.0 g, 92.2 mmol, 1.0 eq.) in anhydrous dichloromethane (150 mL) under nitrogen atmosphere, and the reaction mixture was allowed to stir for 15 min, followed by dropwise addition of acetic anhydride (43.9 mL, 464 mmol, 5.0 eq.) at 0 C. The resulting reaction mixture was stirred for 2 h at 40 C. The resulting reaction mixture was quenched with a saturated aqueous solution of Na2CO3 (500 mL) and extracted with dichloromethane (100 mL × 4). The combined organic extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure, yielding the desired compound B, (Fig. 1A, 15.5 g, 82% yield) as colorless oil. The compound was used as such in the next step without further characterization and confirmation.
	With triethylamine; In ethyl acetate; at 10℃;	3a. N-(4,4-Diethoxybutyl)acetamide4,4-Diethoxybutylamine (3.0 g, 18.61 mmol) and triethylamine (7.85 ml, 55.83 mmol) were dissolved in 250 ml of ethyl acetate. At 100C, acetic anhydride (1.75 ml, 18.61 mmol) was added, and stirring was continued for 2 h. The cooling bath was removed after 1 h. The reaction mixture was concentrated. Yield: 1.526 g. The product was directly reacted further.

Reference： [1]Organic Letters,2009,vol. 11,p. 5142 - 5145
[2]Molecular Pharmacology,2019,vol. 95,p. 269 - 285
[3]Patent: WO2010/3624,2010,A2 .Location in patent: Page/Page column 74
[4]Journal of Medicinal Chemistry,2010,vol. 53,p. 8679 - 8687

24
[ 6346-09-4 ]
[ 943230-31-7 ]
[ 943230-34-0 ]

Yield	Reaction Conditions	Operation in experiment
90.7%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃;	Stir 600 mg (1.78 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, 344.7 mg (2.14 mmol) 4-aminobutyraldehyde-diethylacetal and 0.465 ml (2.67 mmol) DIEA in 5 ml DMF overnight at 80 C. After cooling, purify the mixture directly by preparative RP-HPLC (gradient acetonitrile/water). 746 mg (90.7% of theor.) of the target compound is obtained. LC-MS (Method 2): Rt=2.87 min; m/z=462 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): delta=8.34 (s, 1H), 7.48-7.41 (m, 4H), 7.38-7.30 (m, 3H), 7.13 (d, 2H), 5.12 (t, 1H), 4.40 (t, 1H), 3.35 (s, 3H), 3.55-3.47 (m, 2H), 3.42-3.35 (m, 4H), 1.49-1.38 (m, 4H), 1.09 (t, 6H).

Reference： [1]Patent: US2009/318475,2009,A1 .Location in patent: Page/Page column 12; 20-21

25
[ 6346-09-4 ]
[ 55394-81-5 ]
[ 1190732-30-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3561 - 3571

26
[ 6346-09-4 ]
[ 103-71-9 ]
N-(4,4-diethoxybutyl)-N′-phenylurea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In benzene; at 5 - 20℃; for 6h;	To the solution of 2.03 g (12.6 mmol) of (4,4-diethoxybutyl)amine in 10 mL of benzene 1.50 g (12.6 mmol) of phenylisocyanate was addeddropwise at 5 . Reaction mixture was stirred ad room temperature for 6 h. Solvent wasremoved and residue dried in vacuum (0.01 torr, 5 h) to give 1-(4,4-diethoxybutyl)-3-phenylurea3 as white powder (3.00 g, 85.0%). mp 66-67 . IR (numax, cm-1): 1598, 1637, 2726. 1 NMR(600 MHz, CDCl3) deltaH 1.16 (6, t, 3JHH 7.06 Hz), 1.46-1.62 (4, m), 3.15 (2H, m); 3.44 (2, q,3JHH 7.04 Hz), 3.58 (2, q, 3JHH 7.04 Hz), 4.39 (1H, t, 3JHH 5.45 Hz), 6.96 (1H, t, 3JHH 7.28 Hz),7.20 (2H, t, 3JHH 8.12 Hz), 7.25 (2H, d, 3JHH 7.46 Hz). Anal.calcd for C15H24N2O3 (280.18): C,64.26; H, 8.63; N, 9.99%. Found: , 64.25; , 8.65; N, 10.01%.

Reference： [1]ARKIVOC,2014,vol. 2014,p. 319 - 327
[2]Chemistry of Heterocyclic Compounds,2014,vol. 50,p. 707 - 714
Khim. Geterotsikl. Soedin.,2014,vol. 50,p. 769 - 776,8
[3]Russian Journal of General Chemistry,2009,vol. 79,p. 1163 - 1166

27
[ 6346-09-4 ]
[ 98-59-9 ]
[ 858005-68-2 ]

Yield	Reaction Conditions	Operation in experiment
93%		General procedure: To the cooled solution (5-8) of appropriate sulfonyl chloride (20 mmol) and triethylamine (3.5 ml) in dichloromethane (100 ml) 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 1.
93%		General procedure: 4,4-Diethoxybutan-1-amine (3.4 g,20 mmol) was added to a cooled (5-8) solution of theappropriate sulfonyl chloride (20 mmol) and Et3N (3.5 ml) in CH2Cl2 (100 ml). The reaction mixture was stirred atroom temperature for 12 h, then washed with saturatedNaHCO3 solution (100 ml), the organic layer was separatedand the residual solvents were removed under reducedpressure. N-(4,4-Diethoxybutyl)-4-methylbenzenesulfonamide(1). Yield 6.20 g (93%), yellow oil. 1 NMR spectrum(CDCl3), delta, ppm (J, Hz): 1.19 (6H, t, J = 7.1, 2CH3); 1.54-1.64 (4, m, 22); 2.44 (3, s, 3); 2.94-3.01 (2, m,2); 3.42-3.51 (2, m, 2); 3.58-3.66 (2, m, 2);4.42 (1, t, J = 5.1, ); 4.88 (1, br. s, NH); 7.31 (2, d,J = 8.0, Ar); 7.76 (2, d, J = 8.2, Ar).

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4361 - 4366
[2]Journal of the American Chemical Society,2013,vol. 135,p. 9358 - 9361
[3]Synthetic Communications,2017,vol. 47,p. 44 - 52
[4]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 161 - 166
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 161 - 166,6

28
[ 6346-09-4 ]
[ 5870-38-2 ]
C₁₈H₂₇NO₇ [ No CAS ]
C₂₄H₄₀N₂O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3923 - 3926

29
[ 6346-09-4 ]
[ 5870-38-2 ]
C₁₈H₂₇NO₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3927 - 3930

30
[ 92613-96-2 ]
[ 6346-09-4 ]
[ 1400676-81-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;	B: (R)-Benzyl l-(4,4-diethoxybutylamino)-3-mercapto-3-methyl-l-oxobutan-2- ylcarbamate[00253] To a round bottom flask was added (R)-2-(benzyloxycarbonylamino)-3- mercapto-3-methylbutanoic acid (4.68 g, 16.52 mmol), HOBT (2.53 g, 16.52 mmol), EDC (3.17 g, 16.52 mmol), DCM (50 mL), TEA (2.302 mL, 16.52 mmol) and 4,4- diethoxybutan-1 -amine (2.66 g, 16.52 mmol). The reaction was stirred at rt overnight. The reaction was diluted with DCM (150 mL). The organics was washed with water (2 x 150 mL), saturated aqueous NaCl (100 mL). The organic layer was separated, dried over MgS04, filtered and concentrated to give (R)-benzyl l-(4,4-diethoxybutylamino)-3- mercapto-3 -methyl- l-oxobutan-2-ylcarbamate (6.90 gm, 16.2 mmol, 98% yield) as an oil.

Reference： [1]Patent: WO2012/125622,2012,A1 .Location in patent: Page/Page column 88

31
[ 6346-09-4 ]
[ 1416069-66-3 ]
[ 1416069-67-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 2-hydroxy-pyridine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a stirred solution of 4-((3-(azido(phenyl)methyl)phenoxy)- methyl)benzoic acid (0.5 g, 1.39 mmol) in dimethyl formamide (14 mL) was added l-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.29 g, 1.53 mmol), 2-hydroxypyridine-N-oxide (0.16 g, 1.53 mmol) and triethylamine (0.49 mL. 3.48 mmol). The reaction mixture was stirred at room temperature for 10 minutes. 4-Amino-butyraldehyde diethyl ether (0.27 g, 1.67 mmol) was added and the reaction mixture stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in wo-hexane to afford the title compound as a colourless oil (0.51 g,73%). NMR (400 MHz, CDC13): delta 7.78 (d, J = 8.08 Hz, 2 H); 7.46 (d, J = 7.94 Hz, 2 H); 7.40-7.24 (m, 6 H); 6.94-6.83 (m, 3 H); 6.52 (s, 1 H); 5.67 (s, 1 H); 5.08 (s, 2 H); 4.58-4.48 (m, 1 H); 3.72-3.62 (m, 2 H); 3.56-3.46 (m, 4 H); 1.83-1.69 (m, 4 H); 1.21 (t, J = 7.04 Hz, 6 H).

Reference： [1]Patent: WO2012/168359,2012,A1 .Location in patent: Page/Page column 110; 111

32
[ 141-79-7 ]
[ 6346-09-4 ]
[ 85358-17-4 ]

Yield	Reaction Conditions	Operation in experiment
48%		The compound was prepared as described in J. Chem. Soc, Perkin Trans. 1 1986, 447-453, which is hereby incorporated by reference in its entirety. [00358] 4-Aminobutyraldehyde diethyl acetal (6.4 g, 39.7 mmol) and mesityl oxide (20 ml, 175.2 mmol) were mixed neat and stirred at room temperature for 1 hour. After this time, the reaction mixture was extracted with 2.5 M HC1 and the extract washed with ether. The aqueous layer was heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo to reduce the volume by -50%. The concentrated aqueous layer was cooled on ice and diluted with methylene chloride (-100 ml). The mixture was basified with aqueous potassium hydroxide and the layers separated. The aqueous layer was further extracted with methylene chloride (100 ml) and the combined organic extracts were washed with aqueous potassium carbonate. The organic layer was dried over potassium carbonate, filtered and concentrated. Purification by flash column chromatography, on silica gel, eluting with neat EtOAc provided the product as pale yellow oil, 3.2 g (48% yield). The mixture can also be purified by distillation from K2CO3 (instead of column chromatography) to afford the ketone in a similar yield. [00359] 1H NMR (CDC13, 300 MHz) delta: 3.02 (dt, J = 8.8, 3.6 Hz, 1H), 2.74-2.84 (m, 1H), 2.38-2.54 (m, 3H), 2.09-2.24 (m, 2H), 1.86-2.02 (m, 2H), 1.72-1.82 (m, 1H), 1.45-1.57 (m, 1H), 1.24 (s, 3H), 0.92 (s, 3H).

Reference： [1]Patent: WO2013/152198,2013,A1 .Location in patent: Page/Page column 00357; 00358; 00359
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 2953 - 2961

33
[ 6346-09-4 ]
[ 108-91-8 ]
1-cyclohexyl-3-(4,4-diethoxybutyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		To a solution of appropriate amine (11.2 mmol) in dry CH2Cl2 (11 ml) CDI (2.0 g, 12.3 mmol) wasadded. The mixture was stirred at room temperature for 120 h. To the resulting solution 4,4-diethoxybutyl-1-amine (1.80 g, 11.2 mmol) was added and the reaction mixture was stirred at roomtemperature for additional 72 h. Solvent was evaporated invacuo. Residue was througly washedwith water, filtered and dried in vacuo (2 h, 0.01 torr) to give the title compound 1.

Reference： [1]Tetrahedron,2015,vol. 71,p. 445 - 450

34
[ 6346-09-4 ]
[ 79-44-7 ]
3-(4,4-diethoxybutyl)-1,1-dimethylurea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine; In benzene; at 20℃; for 12h;	A mixture of 3.74 g of 4,4-diethoxybutan-1-amine 1,4.77 g of triethylamine, 2.5 g of dimethylcarbamic acidchloride and 30 mL of benzene was stirred for 2 h. Theresulting precipitate was fi ltered off, and the fi ltrate wasevaporated in vacuum. Yield 4.69 g (87%), yellow oil.1 NMR spectrum (CDCl3), delta, ppm: 1.06 t (6, 3,3JHH = 7.1 Hz), 1.40-1.47 m (2, 2), 1.48-1.54 m(2, 2), 2.75 s (6, 3), 3.07-3.11 m (2, 2),3.33-3.39 m (2, 2), 3.48-3.54 m (2, 2), 4.35 t(1, , 3JHH = 5.4 Hz), 4.74 br. s (1, N). 13 NMRspectrum (CDCl3), delta, ppm: 15.19, 15.21, 25.32, 30.97,36.02, 40.50, 61.22, 102.78, 158.56.
81%	With triethylamine; In benzene; at 5 - 7℃; for 2h;Inert atmosphere; Cooling;	3-(4,4-Diethoxy)-1,1-dimethylurea (IId). N,N-Dimethylcarbamoyl chloride (2.5 g) was added dropwise with cooling (5-7C) under argon to a solution of 3.74 g of 4,4-diethoxy-1-butanamine and4.77 g of triethylamine in 27 mL of benzene. The reaction mixture was stirred under cooling for 2 h. Then the precipitate was filtered off, the filtrate was evaporated in vacuum.

Reference： [1]Russian Journal of General Chemistry,2019,vol. 89,p. 2143 - 2146
Zh. Obshch. Khim.,2019,vol. 89,p. 1606 - 1610,5
[2]Russian Journal of General Chemistry,2015,vol. 85,p. 1779 - 1782
Zh. Obshch. Khim.,2015,vol. 85,p. 1217 - 1220,4

35
[ 1722-12-9 ]
[ 6346-09-4 ]
N-(4,4-diethoxybutyl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In acetonitrile; for 36h;Reflux;	To 1.0 g 2-chloropyrimidine (8.73 mmol) dissolved in30 cm3 of dry acetonitrile 1.40 g 4,4-diethoxybutyl-1-amine (8.73 mmol) and 1.50 g K2CO3 were added. Themixture was refluxed for 36 h. Precipitate was filtered offand solvent was evaporated under reduced pressure.Resulting residue was dried in vacuo (3 h, 1333 Pa) toafford 1.69 g (81 %) 1 as yellow oil. 1H NMR (400 MHzCDCl3): d = 1.18 (t, J = 7.1 Hz, 6H, CH3), 1.64-1.72 (m,4H, CH2), 3.40-3.52 (m, 4H, NCH2, OCH2), 3.58-3.67 (m,2H, OCH2), 4.50 (t, J = 5.5 Hz, 1H, CH), 5.68-5.78 (br.m, 1H, NH), 6.48 (t, J = 4.8 Hz, 1H, CHPyr), 8.24 (d,J = 4.8 Hz, 2H, CHPyr) ppm; 13C NMR (150 MHz,CDCl3): d = 15.7 (CH3), 25.2 (CH2), 31.5 (CH2), 41.6(CH2-N), 61.6 (CH2-O), 103.1 (CH), 110.6 (CHAr), 158.3(CHAr), 162.9 (CAr) ppm; IR (Nujol): v = 781, 803, 990,1062, 1128, 1269, 1371, 1414, 1456, 1535, 1593, 2876,2931, 2975, 3108, 3140, 3276 cm-1

Reference： [1]Monatshefte fur Chemie,2015,vol. 146,p. 1845 - 1849
[2]Chemistry of Heterocyclic Compounds,2019,vol. 55,p. 523 - 528
Khim. Geterotsikl. Soedin.,2019,vol. 55,p. 523 - 528,6

36
[ 6346-09-4 ]
4-(dibromomethyl)benzenecarbaldehyde [ No CAS ]
N-(4,4-diethoxybutyl)-4-(dibromomethyl)benzenecarbimine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In benzene; at 20℃; for 24h;Molecular sieve;	General procedure: A mixture of 0.5 g (1.8 mmol) of 4-(dibromomethyl)benzaldehyde, 0.11 g (1.8 mol) of isopropylamine and 0.2 g of molecular sieves 3A in 10 mL of anhydrous benzene was kept for 24 h at room temperature and filtered. After removal of solvent, 0.44 g (77%) of N-isopropyl-4-(dibromomethyl)benzenecarbimine 13a was obtained as a yellow oily substance.
92%	In benzene; at 20℃; for 24h;Molecular sieve;	General procedure: By analogy with 14a, from aldehyde7 (0.5 g, 1.8 mmol), 4,4-diethoxybutanamine 13d (0.32 g, 1.8mmol), MS (0.2 g) in C6H6 (10 mL) compound 14d in 92 % yield (0.72 g) was obtained, yellow thick oil. 1H NMR (400 MHz, CDCl3, 20): d 1.21 (t, 3JHH = 7.0 Hz, 6H, OCH2Me); 1.43-1.80 (m, 4H, CH2CH2); 3.20-3.70 (m, 6H, OCH2, NCH2); 4.43 (t, 3JHH= 5.0 Hz, 1H, CHO2); 6.59 (s, 1H, CHBr2); 7.52 and 7.68 (d, 3JHH = 8.0 Hz, 4H, C6H4); 8.20 (s, 1H, CH=N). Anal. Calcd for C16H23Br2NO2: C, 45.62; H, 5.51; N, 3.32. Found: C, 45.71; H, 5.64; N,3.13.
92%	In benzene; at 20℃; for 24h;Molecular sieve;	General procedure: The reaction mixture containing 0.5 g (1.8 mmol) of 4-(dibromomethyl)benzenecarbaldehyde (7), 0.11 g (0.0018 mmol) of isopropylamine (12) and 0.2 g of molecular sieves 3 A in 10 mL of dry benzene was thermostated at room temperature for 24 h. N-Isopropyl-4-(dibromomethyl)benzenecarbimine (14) (0.44 g, 77%) in the form of yellow oil was obtained by filtration through the molecular sieves followed by the removal of the solvent in vacuo provided by water jetpump.

Reference： [1]Russian Journal of General Chemistry,2015,vol. 85,p. 2209 - 2211
Zh. Obshch. Khim.,2015,vol. 85,p. 2209 - 2211
[2]Tetrahedron Letters,2016,vol. 57,p. 210 - 212
[3]Russian Chemical Bulletin,2016,vol. 65,p. 191 - 194
Izv. Akad. Nauk, Ser. Khim.,2016,p. 191 - 194,4

37
[ 36603-49-3 ]
[ 6346-09-4 ]
N-(4,4-Diethoxybutyl)-4-((tetrahydro-2H-pyran-2-yl)oxy)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With copper(l) iodide; L-proline; In dimethyl sulfoxide;	Prepared according to General Procedure B from THP-protected bromophenol S1 (10.0 g, 38.9mmol), CuI (1.10 g, 5.84 mmol), L-proline (1.30 g, 11.7 mmol), K2CO3 (10.7 g, 77.8 mmol) andaminobutyraldehyde dimethyl acetal (10.4 mL, 58.4 mmol) in DMSO (63 mL). The reaction wasstirred at 95 C for 18 hours, then was purified by flash chromatography (SiO2, 0.5% Et3N in6:1?1:1, 40-60 C petroleum ether/diethyl ether) to yield the title compound S12 (9.1 g, 27.0 mmol,69% yield) as an orange oil; Rf 0.22 (5:1 40-60 C petroleum ether/diethyl ether); m.p. 137-139 C;numax/cm-1 (film) 3384, 2973, 2940, 2872, 1615, 1510; deltaH (400 MHz, CDCl3) 6.92-6.88 (2H, m), 6.55-6.51 (2H, m), 5.22 (1H, t, J = 3.4 Hz), 4.50 (1H, t, J = 5.3 Hz), 3.98-3.92 (1H, m), 3.68-3.60 (2H, m),3.59-3.54 (1H, m), 3.52-3.45 (2H, m), 3.68 (2H, t, J = 6.7 Hz), 2.02-1.92 (1H, m), 1.85-1.79 (2H,m), 1.73-1.55 (7H, m), 1.20 (6H, t, J = 7.0 Hz); deltaC (100 MHz, CDCl3) 149.0, 143.5, 118.1, 113.6,102.6, 97.6, 61.9, 61.0, 44.4, 31.1, 30.5, 25.2, 24.7, 18.9, 15.2; HRMS (ESI) calculated for C19H32NO4[M+H]+ m/z 338.2326, found 338.2321.

Reference： [1]Synlett,2016,vol. 27,p. 116 - 120

38
[ 6346-09-4 ]
[ 637-60-5 ]
[ 1010-95-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	With zinc(II) chloride; In toluene; at 100℃; for 1h;	In a 250 mL glass bottle, p-tolylhydrazine hydrochloride (5.0 g, 31.5 mmol), ZnCl2 (6.19 g, 38 mmol, 1.2 eq) and 4,4-diethoxybutan-1-amine (8.6 g, 62.9 mmol, 2 eq) were suspended in toluene (80 mL) and allowed to stir at 100 C for 1 h. After completion, the reaction mixture was allowed to cool at RT and then made alkaline with aqueous NaOH (1N, 250 mL). The mixture was extracted with EtOAc (3 × 300 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography (0-8% MeOH in CH2Cl2) to obtain 2-(5-methyl-1H-indol-3-yl)ethanamine which was treated with excess ethanolic HCl and allowed to stir for 10 min. The volatiles were then removed under reduced pressure. The residue obtained was stirred in Et2O and filtered to obtain 2-(5-methyl-1H-indol-3-yl)ethanamine hydrochloride (3.8 g, 57%).1H NMR: (400 MHz, CDCl3) delta 8.06 (br s, 1H), 7.40 (s, 1H), 7.24 (d, 1H), 7.05 (d, 1H), 7.00 (s, 1H), 3.01 (t, 2H), 2.88 (t, 2H), 2.44 (s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5103 - 5109

39
[ 6346-09-4 ]
[ 5446-18-4 ]
[ 94850-28-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sulfuric acid; In water; at 100℃; for 2h;	2,4-Dichlorophenyl)hydrazine hydrochloride (5.0 g, 23.5 mmol) was suspended in 4% aqueous sulphuric acid (150 mL) and 4-amino butyraldehyde diethyl acetal (4.53 g, 28.mmol, 1.2 eq) was added to the suspension. The reaction mixture was heated to 100 C and monitored by LCMS. The reaction was complete after 2 h. The reaction mixture was then cooled to RT and the pH was adjusted to 10-12 with aqueous NaOH (1N, 90 mL). The aqueous layer was extracted with CH2Cl2 (2 × 250 mL). The combined organic layers were dried over anhydrous Na2SO4 filtered and concentrated to obtain 4 g of 2-(5,7-dichloro-1H-indol-3-yl)ethan-1-amine as a semi-solid. To this was added ethanolic HCl (150 mL) until the pH of the solution was 2-3. The solution was then concentrated under vacuum to remove to obtain 2-(5, 7-dichloro-1H-indol-3-yl) ethan-1-amine hydrochloride (4.5 g, 84%).LCMS: 228.02 [M+1]+.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5103 - 5109

40
[ 6346-09-4 ]
[ 98-59-9 ]
2-ethoxy-1-tosylpyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: To a cooled solution (5-8) of 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) and triethylamine (3.5ml) in dichloromethane (100 ml) sulfonyl chloride (20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 2.
58%		General procedure: The appropriate sulfonyl chloride (20 mmol) wasadded with cooling (5-8) to a solution of 4,4-diethoxybutan-1-amine (3.4 g, 20 mmol) and Et3N (3.5 ml) inCH2Cl2 (100 ml). The reaction mixture was stirred at roomtemperature for 12 h. The reaction mixture was thenwashed with saturated aqueous NaHCO3 solution (100 ml),the organic layer was separated, and the solvent wasremoved under reduced pressure.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 44 - 52
[2]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 161 - 166
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 161 - 166,6

41
[ 6346-09-4 ]
[ 594-44-5 ]
N-(4,4-diethoxybutyl)ethanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: To the cooled solution (5-8) of appropriate sulfonyl chloride (20 mmol) and triethylamine (3.5 ml) in dichloromethane (100 ml) 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 1.
90%		General procedure: 4,4-Diethoxybutan-1-amine (3.4 g,20 mmol) was added to a cooled (5-8) solution of theappropriate sulfonyl chloride (20 mmol) and Et3N (3.5 ml) in CH2Cl2 (100 ml). The reaction mixture was stirred atroom temperature for 12 h, then washed with saturatedNaHCO3 solution (100 ml), the organic layer was separatedand the residual solvents were removed under reducedpressure.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 44 - 52
[2]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 161 - 166
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 161 - 166,6

42
[ 6346-09-4 ]
[ 124-63-0 ]
N-(4,4-diethoxybutyl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%		General procedure: To the cooled solution (5-8) of appropriate sulfonyl chloride (20 mmol) and triethylamine (3.5 ml) in dichloromethane (100 ml) 4,4-diethoxybutane-1-amine (3.4 g, 20 mmol) was added. Reaction mixture was stirred at room temperature for 12 h, washed with saturated NaHCO3 solution in water (100 ml). Organic layer was separated, dried over MgSO4 and evaporated to give target compounds 1.
97%		General procedure: 4,4-Diethoxybutan-1-amine (3.4 g,20 mmol) was added to a cooled (5-8) solution of theappropriate sulfonyl chloride (20 mmol) and Et3N (3.5 ml) in CH2Cl2 (100 ml). The reaction mixture was stirred atroom temperature for 12 h, then washed with saturatedNaHCO3 solution (100 ml), the organic layer was separatedand the residual solvents were removed under reducedpressure.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 44 - 52
[2]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 161 - 166
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 161 - 166,6

43
[ 6346-09-4 ]
[ 98-60-2 ]
1-[(4-chlorophenyl)sulfonyl]-2-ethoxypyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With trimethylamine; In dichloromethane; at 5 - 20℃; for 12h;	To a mixture of 4.2 g (20 mmol) of 4-chlorobenzenesulfonyl chloride and 2.5 mL oftrimethylamine in 100 mL of dichloromethane at cooling (5-8 C) was added 3.2 g (20 mmol) of 4,4-diethoxybutan-1-amine. The reaction mixture was stirred at room temperature for 12 h, washed with saturated solution of NaHCO3 (100 mL), the organic layer was separated and evaporated in a vacuum. Yield 5.4 g (93%). 1H NMR spectrum (CDCl3), , ppm: 1.12t (3H, CH3, J 7.0 Hz), 1.38-1.48 m (1H, CH2), 1.69-1.77 m (1H, CH2), 1.81-1.87 m (1H, CH2), 1.91-2.09m (1H, CH2), 3.07-3.15 m (1H, CH2), 3.30-3.39 m(1H, CH2), 3.42-3.50 m (1H, CH2), 3.66-3.72 m (1H, CH2), 5.15-5.19 m (1H, CH), 7.43 d (2H arom, J 8.5 Hz), 7.75 d (2H arom, J 8.5 Hz). 13C NMR spectrum (CDCl3), ppm: 14.98, 14.99, 23.12, 32.76, 47.22, 63.17,90.21, 128.84, 129.25, 137.73, 139.01.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 199 - 202
Zh. Org. Khim.,2017,vol. 53,p. 209 - 212

44
[ 6346-09-4 ]
[ 98-09-9 ]
N-(4,4-diethoxybutyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		General procedure: 4,4-Diethoxybutan-1-amine (3.4 g,20 mmol) was added to a cooled (5-8) solution of theappropriate sulfonyl chloride (20 mmol) and Et3N (3.5 ml) in CH2Cl2 (100 ml). The reaction mixture was stirred atroom temperature for 12 h, then washed with saturatedNaHCO3 solution (100 ml), the organic layer was separatedand the residual solvents were removed under reducedpressure.

Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 161 - 166
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 161 - 166,6

45
[ 6346-09-4 ]
[ 619-21-6 ]
N-(4,4-diethoxybutyl)-3-formylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		To a stirred solution of 3-formylbenzoic acid (0.50 g, 3.3 mmol) in DMF (7 mL) was added DIPEA (0.61 mL, 3.5 mmol) and HATU (1.5 g, 4.0 mmol) and the mixture stirred at room temperature for 15 minutes. 4,4-Diethoxybutan-l -amine (0.43 g, 2.68 mmol) was added and the- stirring continued for a further five hours. The reaction mixture was diluted and washed sequentially with aqueous 1M sodium hydroxide, aqueous 2M sodium hydroxide and brine. The organic phase was dried over magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford the title compound (0.72 g, 93percent). 'H NMR (400 MHz, DMSO-d6); delta 10.08 (s, 1H), 8.71 (dd, J=5.5, 5.5 Hz, 1H), 8.38 (s, 1H), 8.16 (d, J=7.8 Hz, 1H), 8.06 (d, J=7.7 Hz, 1H), 7.71 (dd, J=7.7, 7.7 Hz, 1H), 4.53 - 4.47 (m, 1H), 3.57 (ddd, J=7.0, 9.5, 14.1 Hz, 2H), 3.43 (ddd, J=7.1, 9.5, 14.1 Hz, 2H), 3.31 - 3.27 (m, 2H), 1.58 - 1.54 (m, 4H), 1.11 (dd, J=7.0, 7.0 Hz, 6H).

Reference： [1]Patent: WO2017/93208,2017,A1 .Location in patent: Page/Page column 34

46
[ 6346-09-4 ]
[ 1877-71-0 ]
methyl 3-((4,4-diethoxybutyl)carbamoyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		To a solution of mono-methyl isophthalate (0.50 g, 2.77 mmol) in DMF (5 mL) was added DIPEA (0.55 mL, 3 mmol) and HATU (1.15 g, 3.0 mmol) and the mixture stirred at room temperature for 45 minutes. 4,4-Diethoxybutan-l -amine (0.375 g, 2.3 mmol) was added and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium carbonate (x2) and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford the title compound (0.95 g, >100%). 'HNMR (400 MHz, DMSO-d6); delta 8.69 (dd, J=5.5, 5.5 Hz, 1H), 8.44 (dd, J=1.6, 1.6 Hz, 1H), 8.12 - 8.08 (m, 2H), 7.63 (dd, J=7.8, 7.8 Hz, 1H), 4.51 - 4.47 (m, 1H), 3.90 (s, 3H), 3.56 (ddd, J=7.1, 9.5, 14.1 Hz, 2H), 3.43 (ddd, J=7.0, 9.5, 14.1 Hz, 2H), 3.29 - 3.26 (m, 2H), 1.57 - 1.54 (m, 4H), 1.11 (dd, J=7.1, 7.1 Hz, 6H).

Reference： [1]Patent: WO2017/93208,2017,A1 .Location in patent: Page/Page column 50

47
[ 6346-09-4 ]
[ 5324-30-1 ]
diethyl {2-[(4,4-diethoxybutyl)amino]ethyl}phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In tetrahydrofuran at 70℃; for 24h;	3 Preparation of Compound 3 Description: 50 g (319 mmol, leq) of 4-aminobutyraldehyde diethyl acetal are dissolved at room temperature in 200 ml of THF and 51.5 ml (372 mmol, 1.2 eq) of triethylamine, and then 75.99 g (310 mmol, leq) of diethyl-2-bromethyl phosphonate are added in drops. Next the solution is heated to 70° C. and agitated at this temperature for 24 hours. The solvent is removed on the rotary evaporator. The residue is shaken vigorously with ether and filtered off. The remaining solid is extracted twice more with ether. The ether filtrates are combined and evaporated. The resulting product is a yellow oil, which is used without further purification in the next reaction. (0214) 1H-NMR (DMSO-d6): 4.45 (t, 1H); 3.98 (m, 4H); 3.54 and 3.42 (2m, 2×2H); 2.5-2.8 (m, 4H); 1.90 (m, 2H); 1.25-1.60 (m, 4H); 1.22 (t, 6H); 1.10 (2t, 6H). 31P-NMR (DMSO-d6): 30 ppm. (0215) The intermediate product obtained in the first step is dissolved in 400 ml of THF, mixed with 85.94 ml (620 mmol, 2 eq) of triethylamine and cooled to 0° C. Then 66.11 ml (465 mmol, 1.5 eq) of benzyl chloroformate are added in drops, the cooling is removed and agitation is performed overnight at room temperature. Next the reaction mixture is neutralised with 1 M of hydrochloric acid and the solvent is evaporated off. The residue is shaken with ether and stored overnight in the refrigerator. The resulting solid is separated and thoroughly washed twice more with ether. The ether solutions are combined and evaporated off. The residue is purified by chromatography via a silica gel column. In doing so, initially all impurities are eluted with hexane:acetic ether 2:1 and then the product with acetic ether. (0216) Yield: 85.752 g (60.2%) colourless viscous oil. 1H-NMR (DMSO-d6): 7.34 (m, 5H); 5.07 (s, 2H); 4.44 (m, 1H); 3.94 (m, 4H); 3.6-3.2 (m, 8H); 2.02 (m, 2H); 1.46 (m, 4H); 1.19 (m, 6H); 1.09 (m, 6H). 31P-NMR (DMSO-d6): 28.93 and 28.57 ppm.

Reference： [1]Current Patent Assignee: UGISENSE - US2017/166900, 2017, A1 Location in patent: Paragraph 0212-0216

48
[ 6346-09-4 ]
2-benzyl-6-(methylcarbamoyl)isonicotinic acid [ No CAS ]
6-benzyl-N<SUP>4</SUP>-(4,4-diethoxybutyl)-N<SUP>2</SUP>-methylpyridine-2,4-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 17.25h;Inert atmosphere;	Intermediate 208: 6-Benzyl-N4-f4,4-diethoxybutvn-N2-methylpyridine-2,4- dicarboxamide (1140) (1141) To a mixture of 2-benzyl-6-(methylcarbamoyl)isonicotinic acid (522.1 mg, 1.93 mmol) and HATU (1.071 g, 2.82 mmol) in DMF (7 ml.) was added 4,4-diethoxybutan-l-amine (0.467 ml_, 2.70 mmol, commercially available from, for example, Fluorochem) followed by DIPEA (1.0 ml_, 5.73 mmol). (1142) The mixture was stirred at rt under nitrogen for 17.25 h before being concentrated in vacuo. The mixture was diluted with acetonitrile (7 ml.) and was directly purified by MDAP (3x 3 ml. injection; high pH). The required fractions were combined and the solvent evaporated in vacuo. The residue was redissolved in dichloromethane (approx. 10 ml.) and was transferred to a tarred vial before the solvent was evaporated under a stream of nitrogen and dried in vacuo to give 6-benzyl-N4-(4,4- diethoxybutyl)-N2-methylpyridine-2,4-dicarboxamide (0.651 g, 1.58 mmol, 82 % yield) as a pale yellow gum. (1143) LCMS (2 mins formic) Peak Rt = 1.08 mins, m/z= 414 for [MH]+ *H NMR (400 MHz, CDC ) delta ppm 8.23 (d, 7=1.5 Hz, 1 H) 7.98 - 8.10 (m, 1 H) 7.80 (d, 7=1.5 Hz, 1 H) 7.30 - 7.36 (m, 2 H) 7.22 - 7.29 (m, 3 H) 6.73 - 6.82 (m, 1 H) 4.51 - 4.56 (m, 1 H) 4.23 (s, 2 H) 3.69 (dq, 7=9.3, 7.1 Hz, 2 H) 3.46 - 3.57 (m, 4 H) 3.07 (d, 7=5.1 Hz, 3 H) 1.70 - 1.76 (m, 4 H) 1.21 (t, 7=7.1 Hz, 6 H)

Reference： [1]Patent: WO2017/174621,2017,A1 .Location in patent: Page/Page column 134-135

49
[ 6346-09-4 ]
2-chloro-6-(methylcarbamoyl)isonicotinic acid [ No CAS ]
6-chloro-N₄-(4,4-diethoxybutyl)-N₂-methylpyridine-2,4-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16h;	Intermediate 145: 6-Chloro-N4-(4,4-diethoxybutyl>N2-methylpyridine-2,4- dicarboxamide (0902) (0903) To a solution of 2-chloro-6-(methylcarbamoyl)isonicotinic acid (2 g, 8.85 mmol) and HATU (3.70 g, 9.74 mmol) in DMF (20 mL) was added DIPEA (3.09 mL, 17.71 mmol) followed by 4,4- diethoxybutan-l-amine (1.68 mL, 9.74 mmol). The resulting solution was stirred at rt for 16 h. Water (60 mL) and EtOAc (60 mL) were added and the layers separated. The aqueous layer was further extracted with ethyl acetate (2 x 30 mL). The combined organics were back-extracted with water (2 x 30 mL) and sat. aqueous LiCI (30 mL) and then dried (Na2S04), filtered and concentrated in vacuo to give a dark oil. This was re-dissolved in DCM and directly applied to the top of a 100 g SNAP silica cartridge and purified by SP4 flash column chromatography. The column was eluted with a gradient of 30-70% ethyl acetate in cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the product, 6-chloro-N4-(4,4-diethoxybutyl)-N2-methylpyridine-2,4-dicarboxamide (2.39 g, 6.68 mmol, 75 % yield) as a yellow oil. (0904) LCMS (2 min High pH): Rt = 0.92 min, [MH]- = 356.2.

Reference： [1]Patent: WO2017/174621,2017,A1 .Location in patent: Page/Page column 104

50
[ 6346-09-4 ]
(S)-2-(methylcarbamoyl)-6-(1-phenylethyl)isonicotinic acid [ No CAS ]
(S)-N₄-(4,4-diethoxybutyl)-N₂-methyl-6-(1-phenylethyl)pyridine-2,4-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1.5h;	Intermediate 216: (SV^-(4.4-DiethoxybutylV^-methyl-6-(l- phenylethvQpyridine-2,4-dicarboxamide (1172) To a solution of (5)-2-(methylcarbamoyl)-6-(l-phenylethyl)isonicotinic acid (120.1 mg, 0.42 mmol) and HATU (243.8 mg, 0.64 mmol) in DMF (2 mL) was added 4,4-diethoxybutan-l-amine (0.110 mL, 0.63 mmol) and DIPEA (0.221 mL, 1.27 mmol). The resulting solution was stirred at rt for 1.5 h, after which it was diluted with DMSO (4 mL) and directly purified by MDAP (high pH). The required fractions were evaporated under a stream of nitrogen, redissolved in methanol and combined. This solution was evaporated under a stream of nitrogen and the residue dried in vacuo to give (5)-yV- (4,4-diethoxybutyl)-Ae-methyl-6-(l-phenylethyl)pyridine-2,4-dicarboxamide (152.2 mg, 0.36 mmol, 84 % yield) as a yellow gum. (1173) LCMS (2 min High pH): Rt = 1.14 min, [MH]+ = 428.5.

Reference： [1]Patent: WO2017/174621,2017,A1 .Location in patent: Page/Page column 138-139

51
[ 6346-09-4 ]
(±)-2-(methoxy(phenyl)methyl)-6-(methylcarbamoyl)isonicotinic acid [ No CAS ]
(±)-N4-(4,4-diethoxybutyl)-6-(methoxy(phenyl)methyl)-N2-methylpyridine-2,4-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 4h;	Intermediate 218: (+/ -N 4,4-Diethoxybutyl>6-(methoxy(phenv0methv0- N 2-methyl pyridi ne-2,4-d ica rboxa mide (1179) To a solution of 2-(methoxy(phenyl)methyl)-6-(nnethylcarbannoyl)isonicotinic acid (150 mg, 0.50 mmol) and HATU (209 mg, 0.55 mmol) in DMF (1.5 mL) was added DIPEA (0.174 mL, 1.00 mmol) followed by 4,4-diethoxybutan-l-amine (0.095 mL, 0.55 mmol). The resulting solution was stirred at rt for 2 h. Further HATU (50 mg), DIPEA (43 mu) and 4,4-diethoxybutan-l-amine (24 mu) were added sequentially and the reaction stirred for a further 2 h and then quenched. Water (20 mL) and EtOAc (20 mL) was added and the layers separated. The aqueous layer was further extracted with ethyl acetate (2 x 10 mL). The combined organics were back-extracted with water (2 x 10 mL) and sat. aqueous LiCI (10 mL) and then dried (Na2S04), filtered and concentrated in vacuo to give a dark oil. This was redissolved in DCM and directly applied to the top of a SNAP silica cartridge (10 g) and purified by SP4 flash column chromatography. The column was eluted with a gradient of 30-100% ethyl acetate in cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the product as a yellow oil - N4-(4,4-diethoxybutyl)-6-(methoxy(phenyl)methyl)-N2- methylpyridine-2,4-dicarboxamide (183 mg, 0.41 mmol, 83 % yield) (1180) LCMS (2 min Formic): Rt = 1.07 min, [MH]+ = 444.4. (1181) *H NMR (400 MHz, DMSO-cfe) delta ppm 8.98 (t, 7=5.5 Hz, 1 H) 8.63 (q, 7=4.6 Hz, 1 H) 8.30 (d, 7=1.7 Hz, 1 H) 8.04 (d, 7=1.7 Hz, 1 H) 7.45 - 7.52 (m, 2 H) 7.31 - 7.38 (m, 2 H) 7.23 - 7.30 (m, 1 H) 5.49 (s, 1 H) 4.45 - 4.50 (m, 1 H) 3.55 (dq, 7=9.5, 7.1 Hz, 2 H) 3.42 (dq, 7=9.5, 7.0 Hz, 2 H) 3.37 (s, 3 H) 3.23 - 3.30 (obs. m, 2 H) 2.86 (d, 7=4.9 Hz, 3 H) 1.51 - 1.59 (m, 4 H) 1.10 (t, 7=7.0 Hz, 6 H)

Reference： [1]Patent: WO2017/174621,2017,A1 .Location in patent: Page/Page column 139-140

52
[ 6346-09-4 ]
[ 405-39-0 ]
dibenzyl (6-((4,4-diethoxybutyl)amino)-6-oxohexane-1,5-diyl)(R)-dicarbamate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 538 - 541

53
[ 6346-09-4 ]
[ 1622-32-8 ]
2-ethoxy-1-(vinylsulfonyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In dichloromethane; at 5 - 20℃; for 12h;	To a solution of 3.4 g (20 mmol) of 4,4-diethoxybutane-1-amine in 6 mL of Et3N in 100 mL of CH2Cl2 3.64 g(20 mmol) of 2-chloroethanesulfonyl chloride at 5-8C was added. The reaction mixture was stirred at room temperature for 12 h, then washed with 100 mL of saturated NaHCO3 solution. The organic phase was separated and the solvent was removed in a vacuum.Yield 82%. 1H NMR spectrum (CDCl3), delta, ppm (J,Hz): 1.05 t (3H, CH3, 3JHH = 7.1), 1.61-1.70 m (1H,CH2), 1.80-1.87 m (2H, CH2), 1.92-2.03 m (1H, CH2), 3.07-3.13 m (1H, CH2), 3.22-3.27 m (1H, CH2), 3.34-3.40 m (1H, CH2), 3.50-3.60 m (1H, CH2), 4.94 d (1H,CH, 3JHH = 4.9), 5.86 d (1H, CH2, 3JHH = 10.0), 6.08 d(1H, CH2, 3JHH = 16.6), 6.36 d.d (1H, CH, 3JHH = 16.6,3JHH = 9.9). 13C NMR spectrum (CDCl3), deltaC, ppm:14.92, 22.99, 32.83, 47.00, 63.06, 89.92, 126.93, 134.36

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 131 - 135
Zh. Obshch. Khim.,2018,vol. 88,p. 138 - 142,5
[2]Chemistry and biodiversity,2019,vol. 16
[3]Mendeleev Communications,2019,vol. 29,p. 686 - 687

54
[ 6346-09-4 ]
[ 86-84-0 ]
1-(4,4-diethoxybutyl)-3-(naphthalen-1-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In benzene; at 20℃; for 12h;	To 0.95 g 1-isocyanatonaphthalene (5.62 mmol) dissolved in 20 cm3 of dry benzene 0.90 g 4,4-diethoxybutan-1-amine (5.59 mmol) was added. The mixture was stirred at room temperature for 12 h. The precipitate was filtered off,washed with 10 cm3 benzene, and dried in vacuum(0.01 torr, 4 h, r.t.) to give 6 as white solid. Yield 1.63 g(88%); m.p.: 121-122 C (from ethanol); 1H NMR[600 MHz, (CD3)2SO]: d = 1.11 (6H, t, J = 6.86 Hz,CH3), 1.48-1.52 (2H, m, CH2), 1.56-1.60 (2H, m, CH2),3.14-3.17 (2H, m, CH2), 3.42-3.47 (2H, m, CH2),3.55-3.60 (2H, m, CH2), 4.50 (1H, t, J = 5.49 Hz, CH),6.56 (1H, t, J = 5.48 Hz, NH), 7.41 (1H, t, J = 7.96 Hz,CHAr), 7.49-7.55 (3H, m, CHAr), 7.88 (1H, d,J = 8.23 Hz, CHAr), 7.99 (1H, d, J = 7.68 Hz, CHAr),8.08 (1H, d, J = 8.23 Hz, CHAr), 8.44 (1H, s, NH) ppm;13C NMR [150 MHz, (CD3)2SO]: d = 15.8, 25.6, 31.4,39.5, 61.1, 102.6, 116.9, 121.8, 122.4, 125.8, 126.0, 126.2,126.4, 128.8, 134.2, 135.7, 156.1 ppm; MS (MALDITOF):m/z = 353 ([M+Na]+).

Reference： [1]Monatshefte fur Chemie,2018,vol. 149,p. 535 - 541
[2]Russian Journal of General Chemistry,2019,vol. 89,p. 2143 - 2146
Zh. Obshch. Khim.,2019,vol. 89,p. 1606 - 1610,5

55
[ 3350-78-5 ]
[ 6346-09-4 ]
N-(4,4-diethoxybutyl)-3-methylbut-2-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In chloroform; at 0 - 20℃; for 3h;Inert atmosphere;	General procedure: Under an argon atmosphere, a solution is prepared containing amino acetal (1.2 mmol) and triethylamine (2.0 mmol) in dry chloroform (10 mL). The mixture is cooled to 0 C and a solution of the acid chloride (1 mmol, in 5 mL of CHCl3) is added slowly with stirring. The mixture is allowed to warm to room temperature for 3 h. Following this reaction period, the mixture is extracted twice with chloroform. The organic extracts are then washed with 1 M HCl, with water, and twice with brine solution. After drying over anhydrous sodium sulphate, the organic solvent is removed by reduced pressure and the crude product is subject to column chromatography (SiO2, hexanes:ethyl acetate).

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1932 - 1935

56
[ 6346-09-4 ]
[ 124-38-9 ]
alkyl methacrylate [ No CAS ]
C₁₂H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With Quinuclidine; [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; In toluene; at 40℃; under 760.051 Torr;Irradiation;	General procedure: To a 25 ml oven-dried Schlenk sealing tube containing a magnetic stir bar were added [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 (6.6 mg, 0.006 mmol), quinuclidine (11.1 mg,0.1 mmol), primary alkyl amine (0.3 mmol), acrylate (0.2 mmol) and 0.5 ml oftoluene and tAmOH mixture (1/3, vol/vol). The reaction tube was sealed, frozenby liquid nitrogen for 10 min, and evacuated under vacuum and backfilled withCO2 (balloon) three times through a three-way stopcock. Liquid nitrogen andthe CO2 balloon were then removed. The reaction tube was sealed and allowedto stand at room temperature for 10 min, at which time the plug of the tube wasslowly opened to release the excess CO2 gas. The tube was then resealed and placedapproximately 3 inches away from a Kessil LED illuminator. The reaction mixturewas stirred and irradiated for 24-48 h. The internal temperature was measured tobe approximately 40 C using an infrared thermometer. The crude mixture wasthen concentrated in vacuo and purified by flash chromatography on silica gelwith a 4g column on a Teledyne ISCO CombiFlash Rf+ Lumen instrument usingthe indicated solvent system.

Reference： [1]Nature Chemistry,2018,vol. 10,p. 1037 - 1041

57
[ 6346-09-4 ]
[ 17529-42-9 ]
[ 1620-98-0 ]
{(3,5-di-tert-butyl-4-hydroxyphenyl)-[(4,4-diethoxybutylamino) oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With toluene-4-sulfonic acid In benzene Reflux; Dean-Stark;	General procedure for the synthesis of compounds 4a-4d. General procedure: An equimolar amounts of 4,4-diethoxybutylamine, 3,5-di-tert-butyl-4-hydroxybenzaldehyde (or paraformaldehyde), and dialkyl(aryl) phosphine acid 3a-3d in 60 mL of benzene was refluxed with a Dean-Stark trap in the presence of 0.06 g of p-toluenesulfonic acid. Then 0.12 g of potassium carbonate was added to the reaction mixture, and the mixture was boiled for 10 min, and cooled. The precipitate was filtered off, the organic layer was washed three times with water and dried with MgSO4. After removal of the solvent the desired phosphine oxides were obtained.

Reference： [1]Vagapova; Abdrakhmanova; Burilov; Garifzyanov; Bukharov; Pudovik [Russian Journal of General Chemistry, 2018, vol. 88, # 9, p. 1912 - 1914][Zh. Obshch. Khim., 2018, vol. 88, # 9, p. 1544 - 1546,3]

58
[ 6346-09-4 ]
[ 93-11-8 ]
N-(4,4-diethoxybutyl)naphthalene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In dichloromethane; at 5 - 20℃; for 12h;	General procedure: To a cooled solution of 20 mmol of the appropriate sulfonyl chloride in 100 mL dry CH2Cl2, 3.5 mL of triethylamine (25 mmol) and 3.40 g of 4,4-diethoxybutan-1-amine (20 mmol) were added at 5-8 S. The reaction mixture was stirred at room temperature for 12 h, washed with 100 mL of saturated NaHCO3 solution and 100 mL of distilled water. The organic layer was separated and dried over Na2SO4. The solvent was removed in vacuum. Target compounds 1 were obtained as oils and used without further purification. N-(4,4-Diethoxybutyl)naphthalene-2-sulfonamide 1a Yield 95%, oil. 1H NMR (CDCl3), delta, (J, Hz): 1.11 (6H, t, J=7.0, CH3), 1.53-1.60 (4H, m, CH2), 2.97-3.04 (2H, m, CH2), 3.34-3.43 (2H, m, CH2), 3.49-3.59 (2H, m, CH2), 4.34-4.39 (1H, m, CH), 5.50 (1H, s, NH), 7.34-7.65 (2H, m, Ar-H), 7.84-7.91 (2H, m, Ar-H), 7.91-7.98 (2H, m, Ar-H), 8.45 (1H, s, Ar-H); 13C NMR (CDCl3), delta: 15.22, 24.58, 30.81, 43.14, 61.43, 102.45, 122.39, 127.47, 127.86, 128.29, 128.67, 129.17, 129.44, 132.17, 134.74, 137.00; IR (thin layer), numax, cm-1: 1145, 1650, 3430, 3500; anal. calcd (%) for C18H25NO4S (%): C, 61.51; H, 7.17; N, 3.99; S, 9.12; found: C, 61.38; H, 7.25; N, 3.88; S, 9.08; ESI-TOF, m/z: 390 [M+K]+.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2018,vol. 193,p. 766 - 770

59
[ 574-17-4 ]
[ 6346-09-4 ]
2-(2-acetamidophenyl)-N-(4,4-diethoxybutyl)-2-oxoacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In dichloromethane at 20℃; for 6h;	General procedure for the synthesis of compounds 4-6. General procedure: An equimolar amount of 4,4-diethoxybutan- 1-amine was added dropwise to a solution of 0.5 g of 1-acetylisatin 1-3 in 10 mL of anhydrous methylene chloride on stirring at 20°C. The mixture was stirred for 6 h and evaporated under reduced pressure (15 mm), the residue was treated with diethyl ether, and the white solid was filtered off and dried under reduced pressure (15 mm). 2-(2-Acetamidophenyl)-N-(4,4-diethoxybutyl)-2- oxoacetamide (4). Yield 97%, mp 86°C. IR spectrum, ν, cm-1: 3348, 3285, 3072, 2974, 2931, 2876, 1674, 1655, 1605, 1580, 1524, 1484, 1450, 1372, 1294, 1220, 1155, 1060. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 1.11 t (6H, CH3, 3J = 7.0), 1.52-1.57 m (4H, CH2), 2.08 s (3H, COCH3), 3.20-3.23 m (2H, NCH2), 3.41-3.46 m (2H, OCH2), 3.54-3.59 m (2H, OCH2), 4.48 t (1H, CH, 3J = 5.0), 7.23 d.d (1H, 5-H, 3J = 7.5, 7.5), 7.60-7.65 m (2H, 4-H, 6-H), 7.92 d (1H, 3-H, 3J = 8.2), 8.69 t (1H, 3J = 5.4, NHCH2), 10.59 s (1H, AcNH). 13C NMR spectrum (DMSO-d6), δC, ppm: 191.93 (C=O), 168.70 (C=O), 163.71 (C=O), 138.71, 134.09 (CH), 131.65 (CH), 123.41, 123.25 (CH), 121.29 (CH), 101.89 (CH), 60.54 (CH2), 38.32 (CH2), 30.68 (CH2), 24.11 (COCH3), 24.01 (OCH2), 23.99 (OCH2), 15.25 (OCH2CH3), 15.23 (OCH2CH3). Mass spectrum (MALDI): m/z 351 [M + H]+. Found, %: C 61.58; H 7.36; N 7.90. C18H26N2O5. Calculated, %: C 61.70; H 7.48 N 7.99.

Reference： [1]Bogdanov; Gazizov; Smolobochkin; Mironov [Russian Journal of Organic Chemistry, 2019, vol. 55, # 1, p. 121 - 123][Zh. Org. Khim., 2019, vol. 55, # 1, p. 157 - 159,3]

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P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6346-09-4 ] {[proInfo.proName]}

Quality Control of [ 6346-09-4 ]

Related Doc. of [ 6346-09-4 ]

Product Details of [ 6346-09-4 ]

Calculated chemistry of [ 6346-09-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6346-09-4 ]

Application In Synthesis of [ 6346-09-4 ]

[ 6346-09-4 ] Synthesis Path-Upstream 1~5

[ 6346-09-4 ] Synthesis Path-Downstream 1~59

Related Functional Groups of [ 6346-09-4 ]

Aliphatic Chain Hydrocarbons

Ethers

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6346-09-4 ]