(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 178433045, compound

HRID 872732Notes

Reaction equation

HRID 872732 reaction equation
[NH2:1][CH2:2][C@@H:3]([N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[C:16]([F:18])[C:13]([C:14]#[N:15])=[C:12]([Cl:19])[CH:11]=2)=[N:6]1)[CH3:4].[CH3:20][C:21]1[NH:22][CH:23]=[C:24]([C:26](O)=[O:27])[N:25]=1>>[Cl:19][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][N:5]([C@@H:3]([CH3:4])[CH2:2][NH:1][C:26]([C:24]3[N:25]=[C:21]([CH3:20])[NH:22][CH:23]=3)=[O:27])[N:6]=2)[CH:17]=[C:16]([F:18])[C:13]=1[C:14]#[N:15]

Participants

3

Reactant 2

HCID 67171415(S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 178433052HCID 178433052, compound

Product 1

HCID 178433045HCID 178433045, compoundYield 8.2%

Procedure

(S)—N-(2-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propyl)-2-methyl-1H-imidazole-4-carboxamide was prepared using the method of Example 34(d) starting from (S)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.0 g, 3.59 mmol) and 2-methyl-1H-imidazole-4-carboxylic acid (0.498 g, 3.95 mmol). The product was purified twice by Flash-chromatography (normal phase and reverse phase). Yield 8.2%. 1H-NMR (400 MHz; DMSO): δ 1.45 (d, 3H), 2.27 (s, 3H), 3.50-3.74 (m, 2H), 4.62-4.77 (m, 1H), 7.02 (d, 1H), 7.45 (s, 1H), 7.88-8.04 (m, 4H), 12.11 (s, 1H).

Workup

  1. customThe product was purified twice by Flash-chromatography (normal phase and reverse phase)

Sources & evidence

ORD record
ord-e70db3f963114a1da355ac9ed986d919
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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