(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate → (S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-1-(6-(trifluoromethyl)pyrazin-2-yl)-1H-pyrazole-4-carboxamide hydrochloride

HRID 571883Notes

Reaction equation

HRID 571883 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].C(OC(N1CCO[C@@H](C2C=CC(N)=C([Cl:53])C=2)C1)=O)(C)(C)C>>[ClH:53].[Cl:1][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:31])([F:30])[F:32])[N:24]=2)[CH:22]=1)=[O:17]

Participants

3

Reactant 2

HCID 68325446(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylateHCID 71086874(S)-N-(2-Fluoro-4-(morpholin-2-yl)phenyl)-1-(6-(trifluoromethyl)pyrazin-2-yl)-1H-pyrazole-4-carboxamide hydrochloride

Product 1

HCID 71086955(S)-N-(2-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-3-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (described in example 29a) instead of (+)—(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-783b795f9259498ca77b414a0d2969cf
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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