(S)-N-(2-Fluoro-4-(morpholin-2-yl)phenyl)-1-(6-(trifluoromethyl)pyrazin-2-yl)-1H-pyrazole-4-carboxamide hydrochloride → (S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-1-(6-(trifluoromethyl)pyrazin-2-yl)-1H-pyrazole-4-carboxamide hydrochloride

HRID 571885Notes

Reaction equation

HRID 571885 reaction equation
[ClH:1].F[C:3]1[CH:8]=[C:7]([C@@H:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[CH:19]=[N:20][N:21]([C:23]2[CH:28]=[N:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=2)[CH:22]=1)=[O:17].Cl.[Cl:34]C1C=C(NC(=O)C2C=CN=C(OCC)C=2)C=CC=1[C@H]1OCCNC1>>[ClH:34].[Cl:1][C:8]1[CH:3]=[C:4]([NH:15][C:16]([C:18]2[CH:19]=[N:20][N:21]([C:23]3[CH:28]=[N:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]=3)[CH:22]=2)=[O:17])[CH:5]=[CH:6][C:7]=1[C@@H:9]1[O:14][CH2:13][CH2:12][NH:11][CH2:10]1

Participants

3

Reactant 2

HCID 71086874(S)-N-(2-Fluoro-4-(morpholin-2-yl)phenyl)-1-(6-(trifluoromethyl)pyrazin-2-yl)-1H-pyrazole-4-carboxamide hydrochlorideHCID 71087265(R)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride

Product 1

HCID 71087159(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-1-(6-(trifluoromethyl)pyrazin-2-yl)-1H-pyrazole-4-carboxamide hydrochloride

Procedure

In analogy to example 83, step a) using 1-(6-Trifluoromethyl-pyrazin-2-yl)-1H-pyrazole-4-carboxylic acid (prepared as described in example 125) instead of 2-(trifluoromethyl)-4-pyridinecarboxylic acid (CAS 131747-41-6) and (−)-(S)-2-(4-Amino-2-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (described in example 91) instead of (+)—(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-b94c8d58dfe649669d56135c78ce779b
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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