1-methyl-1H-imidazole-4-carboxylic acid → (S)-N-(1-(3-(3-chloro-4-cyanophenyl)-4-cyano-1H-pyrazol-1-yl)propan-2-yl)-1-methyl-1H-imidazole-4-carboxamide

HRID 872873Notes

Reaction equation

HRID 872873 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.[NH2:10][C@@H:11]([CH3:29])[CH2:12][N:13]1[CH:17]=[C:16]([C:18]#[N:19])[C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([Cl:28])[CH:21]=2)=[N:14]1>>[Cl:28][C:22]1[CH:21]=[C:20]([C:15]2[C:16]([C:18]#[N:19])=[CH:17][N:13]([CH2:12][C@@H:11]([NH:10][C:7]([C:5]3[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=3)=[O:9])[CH3:29])[N:14]=2)[CH:25]=[CH:24][C:23]=1[C:26]#[N:27]

Participants

3

Reactant 2

HCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 70656272(S)-1-(2-aminopropyl)-3-(3-chloro-4-cyanophenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 67170037(S)-N-(1-(3-(3-chloro-4-cyanophenyl)-4-cyano-1H-pyrazol-1-yl)propan-2-yl)-1-methyl-1H-imidazole-4-carboxamideYield 34.1%

Procedure

The title compound was prepared using the method of Example 34(d) starting from 1-methyl-1H-imidazole-4-carboxylic acid (53.0 mg, 0.420 mmol) and (S)-1-(2-aminopropyl)-3-(3-chloro-4-cyanophenyl)-1H-pyrazole-4-carbonitrile (100 mg, 0.350 mmol). The product was purified by recrystallization from diethyl ether and diethyl ether/ethanol, respectively. Finally the product was also run through flash chromatography. Yield 34.1%. 1H-NMR (400 MHz; DMSO-d6): δ 1.15 (d, 3H), 3.67 (s, 3H), 4.36-4.51 (m, 3H), 7.56 (d, 1H), 7.69 (d, 1H), 7.98 (dd, 1H), 8.04-8.10 (m, 2H), 8.15 (dd, 1H), 8.69 (s, 1H).

Workup

  1. customThe product was purified by recrystallization from diethyl ether and diethyl ether/ethanol

Sources & evidence

ORD record
ord-501bd087a4f04402b4c1cc2c3ecfe0f0
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…