2-(1-(Tert-butyldiphenylsilyloxy)ethyl)thiazole-4-carboxylic acid → 2-(1-(tert-butyldiphenylsilyloxy)ethyl)-N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)thiazole-4-carboxamide

HRID 872860Notes

Reaction equation

HRID 872860 reaction equation
[Si:1]([O:18][CH:19]([C:21]1[S:22][CH:23]=[C:24]([C:26]([OH:28])=O)[N:25]=1)[CH3:20])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C@@H:30]([CH3:46])[CH2:31][N:32]1[CH:36]=[CH:35][C:34]([C:37]2[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[C:39]([Cl:45])[CH:38]=2)=[N:33]1>>[Si:1]([O:18][CH:19]([C:21]1[S:22][CH:23]=[C:24]([C:26]([NH:29][C@@H:30]([CH3:46])[CH2:31][N:32]2[CH:36]=[CH:35][C:34]([C:37]3[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[C:39]([Cl:45])[CH:38]=3)=[N:33]2)=[O:28])[N:25]=1)[CH3:20])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 671683752-(1-(Tert-butyldiphenylsilyloxy)ethyl)thiazole-4-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 706541322-(1-(tert-butyldiphenylsilyloxy)ethyl)-N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)thiazole-4-carboxamide

Procedure

The title compound was prepared using the method of Example 34(d) starting from 2-(1-(tert-butyldiphenylsilyloxy)ethyl)thiazole-4-carboxylic acid (326 mg, 0.792 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (105 mg, 0.403 mmol). After extraction, based on the LC-MS data, the product was estimated to be pure enough for the next step. LC-MS: [M+1]=655.30.

Workup

  1. extractionAfter extraction

Sources & evidence

ORD record
ord-80208f31bbab458dbd2dd6ac0634548a
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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