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

HRID 491643Notes

Reaction equation

HRID 491643 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

4

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 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.

Workup

  1. customa white solid formed
  2. customThe MeOH was removed under reduced pressure
  3. additionthe residue was diluted with 10% aq. NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with 10% aq. NaHCO3
  6. extractionthe organic layers were extracted with CH2Cl2
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was further purified by column chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0ad791e045f544a6942a1c09ff9c00d8
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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