(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → (R)-N-(2-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propyl)-2-(2-hydroxypropan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide

HRID 1409449Notes

Reaction equation

HRID 1409449 reaction equation
[OH:1][C:2]([C:5]1[N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)([CH3:4])[CH3:3].[NH2:21][CH2:22][C@H:23]([N:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:37]=[C:36]([F:38])[C:33]([C:34]#[N:35])=[C:32]([Cl:39])[CH:31]=2)=[N:26]1)[CH3:24]>>[Cl:39][C:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[CH:29][N:25]([C@H:23]([CH3:24])[CH2:22][NH:21][C:10]([C:8]3[N:9]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=3)=[O:12])[N:26]=2)[CH:37]=[C:36]([F:38])[C:33]=1[C:34]#[N:35]

Participants

3

Reactant 2

HCID 70981642(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 709821532-(2-hydroxypropan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 86714663(R)-N-(2-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propyl)-2-(2-hydroxypropan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-(2-hydroxypropan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (1.43 mmol, 430 mg) and (R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.43 mmol, 400 mg). The product was purified by flash-chromatography. Yield 410 mg. LC-MS: [M+1]=561.21.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-f644663c783c4e4da62e69d5f21a4b9e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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