2-chloro-6-(trifluoromethyl)-1H-benzimidazole → {5-Chloro-6-[(3R)-3-methyl-4-(5-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-methanol

HRID 730859Notes

Reaction equation

HRID 730859 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][OH:16])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH3:14])[CH2:9]1.Cl[C:18]1[NH:22][C:21]2[CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=[CH:26][C:20]=2[N:19]=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][OH:16])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:18]2[NH:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:21]=3[N:22]=2)[C@H:10]([CH3:14])[CH2:9]1

Participants

4

Reactant 2

HCID 3379052-chloro-6-(trifluoromethyl)-1H-benzimidazoleHCID 11550484{5-Chloro-6-[(3R)-3-methylpiperazin-1-yl]pyridin-3-yl}methanol

Product 1

HCID 178461536{5-Chloro-6-[(3R)-3-methyl-4-(5-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-methanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of {5-chloro-6-[(3R)-3-methyl-piperazin-1-yl]-pyridin-3-yl}-methanol from step (a) above (96 mg, 0.4 mmol) and 2-chloro-6-trifluoromethyl-1H-benzoimidazole (71 mg, 0.32 mmol, Example 1c) in dioxane (2 mL) reacted under the conditions of Example 3c to give the title compound. MS (ESI, pos. ion) m/z: 426 (M+1).

Workup

  1. customreacted under the conditions of Example 3c

Sources & evidence

ORD record
ord-eac757a8f03949f8aa98c12e39baa583
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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