5-amino-1-phenyl-1H-pyrazole-3-carbonitrile → 2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-methoxy-5-(pyridin-2-yl)benzamide

HRID 522107Notes

Reaction equation

HRID 522107 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[C:22]([C:31]#[N:32])[CH:21]=1>>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:7][C:3]=1[C:4]([NH:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:23]=[C:22]([C:31]#[N:32])[CH:21]=1)=[O:6]

Participants

3

Reactant 2

HCID 177636545-amino-1-phenyl-1H-pyrazole-3-carbonitrileHCID 1184970602-Chloro-4-methoxy-5-(pyridin-2-yl)benzoic acid

Product 1

HCID 1184970422-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-methoxy-5-(pyridin-2-yl)benzamide

Procedure

The title compound was prepared according to the method described for Example 99 using 2-chloro-4-methoxy-5-(pyridin-2-yl)benzoic acid (Preparation 26) and 5-amino-1-phenyl-1H-pyrazole-3-carbonitrile (Preparation 53). The residue was purified using reverse phase chromatography eluting with 5-60% MeCN (with 0.1% formic acid) in water (with 0.1% formic acid).

Workup

  1. customThe residue was purified
  2. washeluting with 5-60% MeCN (with 0.1% formic acid) in water (with 0.1% formic acid)

Sources & evidence

ORD record
ord-e59ee52d12bd42b78ba11cddba0cbe70
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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