(5-Chloro-6-(piperazin-1-yl)pyridin-3-yl)methanol → (5-Chloro-6-{4-[5-(trifluoromethyl)-7-(3,4,5-trifluorophenyl)-1H-benzimidazol-2-yl]piperazin-1-yl}pyridin-3-yl)methanol

HRID 730771Notes

Reaction equation

HRID 730771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Cl[C:17]1[NH:21][C:20]2[CH:22]=[C:23]([C:35]([F:38])([F:37])[F:36])[CH:24]=[C:25]([C:26]3[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=3)[C:19]=2[N:18]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][OH:15])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:17]2[NH:18][C:19]3[C:25]([C:26]4[CH:27]=[C:28]([F:34])[C:29]([F:33])=[C:30]([F:32])[CH:31]=4)=[CH:24][C:23]([C:35]([F:38])([F:36])[F:37])=[CH:22][C:20]=3[N:21]=2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 11514124(5-Chloro-6-(piperazin-1-yl)pyridin-3-yl)methanolHCID 116388672-chloro-6-(trifluoromethyl)-4-(3,4,5-trifluorophenyl)-1H-benzoimidazole

Product 1

HCID 178519828(5-Chloro-6-{4-[5-(trifluoromethyl)-7-(3,4,5-trifluorophenyl)-1H-benzimidazol-2-yl]piperazin-1-yl}pyridin-3-yl)methanol

Procedure

The piperazine from step (a) above (114 mg, 0.5 mmol) reacted with 2-chloro-6-(trifluoromethyl)-4-(3,4,5-trifluorophenyl)-1H-benzoimidazole (140 mg, 0.4 mmol, Example 51b) under the conditions of Example 3c to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 542 (M+1).

Sources & evidence

ORD record
ord-96fed81285fd44b5a39d96fc353fbb64
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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