1-(4-Methylpiperazin-1-yl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)prop-2-en-1-one → N-(2-Dimethylaminoethyl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylamide

HRID 644545Notes

Reaction equation

HRID 644545 reaction equation
COC(=O)C=CC1C2N(C3C=CC=CC=3)C=NC=2C=C(C(F)(F)F)C=1.[CH3:26][N:27]1[CH2:32]C[N:30]([C:33](=[O:55])[CH:34]=[CH:35][C:36]2[C:44]3[N:43]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH:42]=[N:41][C:40]=3[CH:39]=[C:38]([C:51]([F:54])([F:53])[F:52])[CH:37]=2)[CH2:29][CH2:28]1>>[CH3:32][N:27]([CH3:26])[CH2:28][CH2:29][NH:30][C:33](=[O:55])[CH:34]=[CH:35][C:36]1[C:44]2[N:43]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:42]=[N:41][C:40]=2[CH:39]=[C:38]([C:51]([F:52])([F:54])[F:53])[CH:37]=1

Participants

3

Reactant 2

HCID 674849301-(4-Methylpiperazin-1-yl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)prop-2-en-1-oneHCID 674849573-(3-Phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylic acid methyl ester

Product 1

HCID 67487509N-(2-Dimethylaminoethyl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylamideYield 5%

Procedure

This was prepared from 3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylic acid methyl ester in a similar manner to 1-(4-methylpiperazin-1-yl)-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)prop-2-en-1-one. The oily residue was purified by flash chromatography over silica gel (eluted with dichloromethane/methanol 2-5% gradient) to afford the title compound as a white solid (29 mg, 5%), m/z 403.4 (M+H)+.

Workup

  1. customThe oily residue was purified by flash chromatography over silica gel (eluted with dichloromethane/methanol 2-5% gradient)

Sources & evidence

ORD record
ord-bd47f61c56ed464fa600d70d232b4547
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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