2-(1H-pyrrol-1-yl)aniline → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-N-[2-(1H-pyrrol-1-yl)phenyl]-2-pyrrolidinecarboxamide

HRID 1745054Notes

Reaction equation

HRID 1745054 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])(C)(C)C.[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][C:30](C(Cl)=O)=[CH:29][CH:28]=1.[N:42]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[NH2:53])[CH:46]=[CH:45][CH:44]=[CH:43]1>>[C:36]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:37]=[CH:38][C:39]([C:6]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:10][C@H:9]2[C:24]([NH:53][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2[N:42]2[CH:46]=[CH:45][CH:44]=[CH:43]2)=[O:26])=[O:7])=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 801232-(1H-pyrrol-1-yl)anilineHCID 841514-Phenylbenzoyl chlorideHCID 131725417(2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725436(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-N-[2-(1H-pyrrol-1-yl)phenyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid, [1,1′-biphenyl]-4-carbonyl chloride, and 2-(1H-pyrrol-1-yl)phenylamine the title compound was obtained in 54% purity by LC/MS. MS(ESI+): m/z=623.6.

Sources & evidence

ORD record
ord-75d98c9a17544d628adc84c4c8f490c7
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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