3-Amino-1-propanol → HCID 178446475, compound

HRID 2373716Notes

Reaction equation

HRID 2373716 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:27][C:28](=[O:37])[NH:29][C:30](=[NH:36])[N:31]2[CH:35]=[CH:34][CH:33]=N2)=[C:10]([C:13]2[CH:26]=[CH:25][C:16]([C:17]([NH:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:18])=[CH:15][CH:14]=2)[S:11][CH:12]=1.NCCC[OH:42].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:27][C:28]([NH:29][C:30]([NH:31][CH2:35][CH2:34][CH2:33][OH:42])=[NH:36])=[O:37])=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH:20]([CH2:21][CH3:22])[CH2:23][CH3:24])=[O:18])=[CH:25][CH:26]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 1405048704-[4-(2-chlorophenyl)-3-[2-oxo-2-(pyrazole-1-carboximidoylamino)ethyl]thiophen-2-yl]-N-pentan-3-ylbenzamide

Product 1

HCID 178446475HCID 178446475, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(2-chloro-phenyl)-3-{[(imino-pyrazol-1-yl-methyl)-carbamoyl]-methyl}-thiophen-2-yl)-N-(1-ethyl-propyl)-benzamide (0.87 g, 0.16 mmol) in CH2Cl2 (2 mL) was added 3-aminopropanol (0.037 g, 0.040 mL, 0.50 mmol) and diisopropyl ethylamine (0.064 g, 0.087 mL, 0.50 mmol). The solution was stirred overnight at RT. The solvent was removed and the product purified by flash chromatography (15:1 CHCl3:MeOH) to yield 4-[4-(2-chlorophenyl)-3-(2-{[[(3-hydroxypropyl)amino](imino)methyl]amino}-2-oxoethyl)thien-2-yl]-N-(1-ethylpropyl)benzamide (0.047 g) as a white solid. mp 109-110° C. MS (ES) m/z 541.12 ([M+H]+); Anal. Calcd for C28H33ClN4O3S.0.60 H2O: C, 60.93; H, 6.25; N, 10.15. Found: C, 60.57; H, 6.07; N, 10.02.

Workup

  1. customThe solvent was removed
  2. customthe product purified by flash chromatography (15:1 CHCl3:MeOH)

Sources & evidence

ORD record
ord-eecedded94314f64a9c7005113cea556
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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