Diisopropylethylamine → 4-[4-(2-chlorophenyl)-3-[2-oxo-2-(pyrazole-1-carboximidoylamino)ethyl]thiophen-2-yl]-N-pentan-3-ylbenzamide

HRID 2373715Notes

Reaction equation

HRID 2373715 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]([OH:30])=O)=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)[S:11][CH:12]=1.Cl.[N:32]1([C:37]([NH2:39])=[NH:38])[CH:36]=[CH:35][CH:34]=[N:33]1.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](=[O:30])[NH:39][C:37](=[NH:38])[N:32]2[CH:36]=[CH:35][CH:34]=[N:33]2)=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 69200552[4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid

Product 1

HCID 1405048704-[4-(2-chlorophenyl)-3-[2-oxo-2-(pyrazole-1-carboximidoylamino)ethyl]thiophen-2-yl]-N-pentan-3-ylbenzamideYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid (0.125 g, 0.282 mmol) was dissolved in CH2Cl2 (2 mL) and carbonyldiimidizole (0.229 g, 1.41 mmol) was added. The solution was stirred under argon at room temperature for 30 min. 1-H-Pyrazole-1-carboxamidine hydrochloride (0.413 g, 2.82 mmol) and diisopropyl ethylamine (0.737 mL, 4.23 mmol) were added to the solution and stirred overnight. The solvent was removed and the mixture was absorbed onto silica gel and purified by flash chromatography (20:1 CHCl3:MeOH) to yield 4-(4-(2-chloro-phenyl)-3-{[(imino-pyrazol-1-yl-methyl)-carbamoyl]-methyl}-thiophen-2-yl)-N-(1-ethyl-propyl)-benzamide (0.087 g) as a white solid.

Workup

  1. additioncarbonyldiimidizole (0.229 g, 1.41 mmol) was added
  2. stirringstirred overnight
  3. customThe solvent was removed
  4. customthe mixture was absorbed onto silica gel
  5. custompurified by flash chromatography (20:1 CHCl3:MeOH)

Sources & evidence

ORD record
ord-de8301eb53a24729abf95b5782458fda
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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