Piperazin-2-one → 4-[1-(2-Chloro-4-pyridyl)-5-[3-(difluoromethoxy)-5-fluoro-phenyl]pyrazole-3-carbonyl]piperazin-2-one

HRID 930087Notes

Reaction equation

HRID 930087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[CH:18]=3)[N:15]=[C:14]([C:24]([OH:26])=O)[CH:13]=2)[CH:5]=[C:6]([O:8][CH:9]([F:11])[F:10])[CH:7]=1.ClC1C=C(C2N(C3C=NC=CC=3)N=C(C([N:48]3[CH2:53][CH2:52][NH:51][C:50](=[O:54])[CH2:49]3)=O)C=2)C=C(F)C=1.O=C1CNCCN1>>[Cl:23][C:19]1[CH:18]=[C:17]([N:16]2[C:12]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([O:8][CH:9]([F:10])[F:11])[CH:5]=3)=[CH:13][C:14]([C:24]([N:48]3[CH2:53][CH2:52][NH:51][C:50](=[O:54])[CH2:49]3)=[O:26])=[N:15]2)[CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 3

HCID 231360Piperazin-2-oneHCID 715765334-[5-(3-Chloro-5-fluoro-phenyl)-1-(3-pyridyl)pyrazole-3-carbonyl]piperazin-2-oneHCID 896099575-(3-Fluoro-5-difluoromethoxyphenyl)-1-(2-chloropyridin-4-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 865742634-[1-(2-Chloro-4-pyridyl)-5-[3-(difluoromethoxy)-5-fluoro-phenyl]pyrazole-3-carbonyl]piperazin-2-one

Procedure

40 mg (0.10 mmol) of the compound of Example 53A is reacted analogously to the synthesis of the compound of Example 4 with 11 mg (0.11 mmol) of 2-oxopiperazine. 39 mg (80% of theory) of the title compound is obtained.

Sources & evidence

ORD record
ord-bea88e0329b14553beb5b1f69399e789
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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