1-(4-Cyanophenyl)-1H-pyrazole-4-carboxylic acid → (S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-1-(4-cyanophenyl)-1H-pyrazole-4-carboxamide hydrochloride

HRID 571867Notes

Reaction equation

HRID 571867 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.[Cl:18][C:19]1[CH:20]=[C:21]([NH:31]C(=O)C2C=CN=C(OCC)C=2)[CH:22]=[CH:23][C:24]=1[C@H:25]1[O:30][CH2:29][CH2:28][NH:27][CH2:26]1>>[ClH:18].[Cl:18][C:19]1[CH:20]=[C:21]([NH:31][C:14]([C:12]2[CH:11]=[N:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[CH:13]=2)=[O:16])[CH:22]=[CH:23][C:24]=1[C@@H:25]1[O:30][CH2:29][CH2:28][NH:27][CH2:26]1

Participants

3

Reactant 2

HCID 432594251-(4-Cyanophenyl)-1H-pyrazole-4-carboxylic acidHCID 71087265(R)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride

Product 1

HCID 71087096(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-1-(4-cyanophenyl)-1H-pyrazole-4-carboxamide hydrochloride

Procedure

In analogy to example 83, step a) using 1-(4-cyanophenyl)-1H-Pyrazole-4-carboxylic acid (CAS 1152945-21-5) 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 (preparation described in example 91) instead of (+)-(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester. Yellow solid. MS (ISP): 408.2 ([M+H]+)

Sources & evidence

ORD record
ord-186ae80c13da4a30af4b73f42a4c1cb5
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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