Piperazin-2-one → 4-{[5-(3-Chloro-4-fluorophenyl)-4-(3-chloro-5-fluorophenyl)furan-2-yl]carbonyl}piperazin-2-one

HRID 2190136Notes

Reaction equation

HRID 2190136 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[O:41][C:40]([C:42](O)=[O:43])=[CH:39][C:38]=2[C:45]2[CH:50]=[C:49]([F:51])[CH:48]=[C:47]([Cl:52])[CH:46]=2)[CH:33]=[CH:34][C:35]=1[F:36].N1CCNCC1=O>>[Cl:29][C:30]1[CH:31]=[C:32]([C:37]2[O:41][C:40]([C:42]([N:22]3[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]3)=[O:43])=[CH:39][C:38]=2[C:45]2[CH:50]=[C:49]([F:51])[CH:48]=[C:47]([Cl:52])[CH:46]=2)[CH:33]=[CH:34][C:35]=1[F:36]

Participants

4

Reactant 3

HCID 231360Piperazin-2-oneHCID 580647965-(3-Chloro-4-fluorophenyl)-4-(3-chloro-5-fluorophenyl)furan-2-carboxylic acidHCID 580648004-{[4-(3-Chlorophenyl)-5-(4-fluorophenyl)furan-2-yl]carbonyl}piperazin-2-one

Product 1

HCID 580647714-{[5-(3-Chloro-4-fluorophenyl)-4-(3-chloro-5-fluorophenyl)furan-2-yl]carbonyl}piperazin-2-one

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 21A. Instead of 1.5 equivalents of piperazin-2-one, 1.1 equivalents are used. 33.0 mg (53% of theory) of the title compound are obtained.

Sources & evidence

ORD record
ord-b19f8b2d072248d5b8cc5d0225abe0e2
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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