(S)-2-((tert-Butyl dimethylsilyloxy)methyl)-N-(1-(3-(3-chloro-4-cyano phenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide → (S)-N-(1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(hydroxymethyl)-1H-imidazole-4-carboxamide hydrochloride

HRID 1409429Notes

Reaction equation

HRID 1409429 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11](COCC[Si](C)(C)C)[CH:12]=[C:13]([C:15]([NH:17][C@@H:18]([CH3:34])[CH2:19][N:20]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([Cl:33])[CH:26]=3)=[N:21]2)=[O:16])[N:14]=1)(C(C)(C)C)(C)C>Cl>[ClH:33].[Cl:33][C:27]1[CH:26]=[C:25]([C:22]2[CH:23]=[CH:24][N:20]([CH2:19][C@@H:18]([NH:17][C:15]([C:13]3[N:14]=[C:10]([CH2:9][OH:8])[NH:11][CH:12]=3)=[O:16])[CH3:34])[N:21]=2)[CH:30]=[CH:29][C:28]=1[C:31]#[N:32]

Participants

3

Reactant 1

HCID 86714657(S)-2-((tert-Butyl dimethylsilyloxy)methyl)-N-(1-(3-(3-chloro-4-cyano phenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide

Product 1

HCID 178461750(S)-N-(1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(hydroxymethyl)-1H-imidazole-4-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-2-((tert-Butyldimethylsilyloxy)methyl)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide (0.4 g, 15.9 mmol) in 6 N HCl (25 ml) was stirred at 45° C. for 24 h. The resulting mixture was evaporated completely and triturated twice from diethyl ether. In the end all precipitates were combined. Yield 200 mg. 1H-NMR (400 MHz; DMSO-d6): δ 1.19 (d, 3H), 4.31-4.34 (m, 3H), 4.68 (s, 2H), 6.93 (s, 1H), 7.89-7.95 (m, 3H), 8.05 (s, 1H), 8.30 (s, 1H), 9.15 (d, 1H), 14.8 (bs, 1H).

Workup

  1. customThe resulting mixture was evaporated completely
  2. customtriturated twice from diethyl ether

Sources & evidence

ORD record
ord-7f4e09bd56834c5a8288a56edb812639
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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