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

HRID 522106Notes

Reaction equation

HRID 522106 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:18][C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:22]=[C:21]([C:30]#[N:31])[CH:20]=1>>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([NH:18][C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:22]=[C:21]([C:30]#[N:31])[CH:20]=1)=[O:6]

Participants

3

Reactant 2

HCID 177636545-amino-1-phenyl-1H-pyrazole-3-carbonitrileHCID 1184971152-Chloro-4-fluoro-5-(pyridin-2-yl)benzoic acid

Product 1

HCID 1184971802-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-4-fluoro-5-(pyridin-2-yl)benzamide

Procedure

The title compound was prepared according to the method described for Example 99 using 2-chloro-4-fluoro-5-(pyridin-2-yl)benzoic acid (Preparation 22) and 5-amino-1-phenyl-1H-pyrazole-3-carbonitrile (Preparation 53). The residue was purified using silica gel column chromatography eluting with 10% MeOH in EtOAc followed by a second chromatography eluting with 50% EtOAc in heptanes.

Workup

  1. customThe residue was purified
  2. washeluting with 10% MeOH in EtOAc
  3. washeluting with 50% EtOAc in heptanes

Sources & evidence

ORD record
ord-aba6ffb22bd0441cbac001e10e327622
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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