Piperazin-2-one → 3-{3-(3-Chloro-5-fluorophenyl)-5-[(3-oxopiperazin-1-yl)carbonyl]furan-2-yl}benzenecarbonitrile

HRID 2190137Notes

Reaction equation

HRID 2190137 reaction equation
ClC1C=C(C2C=C(C([N:22]3[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]3)=O)OC=2C2C=CC(F)=CC=2)C=CC=1.[Cl:29][C:30]1[CH:31]=[C:32]([C:37]2[CH:38]=[C:39]([C:50](O)=[O:51])[O:40][C:41]=2[C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([C:48]#[N:49])[CH:43]=2)[CH:33]=[C:34]([F:36])[CH:35]=1.N1CCNCC1=O>>[Cl:29][C:30]1[CH:31]=[C:32]([C:37]2[CH:38]=[C:39]([C:50]([N:22]3[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]3)=[O:51])[O:40][C:41]=2[C:42]2[CH:43]=[C:44]([C:48]#[N:49])[CH:45]=[CH:46][CH:47]=2)[CH:33]=[C:34]([F:36])[CH:35]=1

Participants

4

Reactant 3

HCID 231360Piperazin-2-oneHCID 580647984-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acidHCID 580648004-{[4-(3-Chlorophenyl)-5-(4-fluorophenyl)furan-2-yl]carbonyl}piperazin-2-one

Product 1

HCID 468325883-{3-(3-Chloro-5-fluorophenyl)-5-[(3-oxopiperazin-1-yl)carbonyl]furan-2-yl}benzenecarbonitrile

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 6 starting with the compound from Example 20A. Instead of 1.5 equivalents of piperazin-2-one, 1.1 equivalents are used. 55.0 mg (89% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-818b0ddb6c9542a9ad9092a60f228e55
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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