Methanol → (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylsulfonylpyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21](SC)[N:20]=4)=[CH:17][C:11]=3[N:10]=2)=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28].O[O:32][S:33]([O-:35])=O.[K+].[CH3:37]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([S:33]([CH3:37])(=[O:35])=[O:32])[N:20]=4)=[CH:17][C:11]=3[N:10]=2)=[CH:4][C:3]=1[C:27]([F:30])([F:28])[F:29]

Participants

Reactant 3

HCID 887Methanol

HCID 23707502Potassium hydroxy sulfite

HCID 178503457HCID 178503457, compound

Product 1

HCID 178504847(4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylsulfonylpyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine

Procedure

To a solution of (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylsulfanyl-pyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine (Step A, 280 mg, 0.6 mmol, 1.0 eq.) in MeOH (10 mL) was added dropwise an aqueous solution (10 mL) of Oxone® (1.14 g, 1.8 mmol, 3.0 eq.), and a white solid formed. The reaction was stirred for 4 h at RT. The MeOH was removed under reduced pressure, the residue was diluted with 10% aq. NaHCO3 and extracted with CH2Cl2. The organic layer was washed with 10% aq. NaHCO3 and the organic layers were extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and concentrated. The crude was further purified by column chromatography (0-100% EtOAc/hexanes) to yield (4-chloro-3-trifluoromethyl-phenyl)-[5-(2-methylsulfonylpyrimidin-4-yloxy)-1H-benzimidazol-2-yl]-amine. MS m/z=484.0 (M+H)+; MW Calc'd for C19H13ClF3N5O3S: 483.86.