Chloroform → N-(4-Trifluoromethyl-3-(5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)benzyl)-2-methylpropane-2-sulfonamide

HRID 1258731Notes

Reaction equation

HRID 1258731 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][NH:8][S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])=[CH:5][C:4]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([N:29]3[CH2:34][CH2:33][CH:32]([C:35]([F:38])([F:37])[F:36])[CH2:31][CH2:30]3)[C:26]([Cl:28])=[CH:27][C:20]=2[N:19]=1.ClC1C=C(C=CC=1)C(OO)=[O:46].C(Cl)(Cl)Cl.P(Br)(Br)Br>[Cl-].[Na+].O.O.C(Cl)Cl>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][NH:8][S:9]([C:11]([CH3:12])([CH3:14])[CH3:13])(=[O:46])=[O:10])=[CH:5][C:4]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([N:29]3[CH2:30][CH2:31][CH:32]([C:35]([F:37])([F:36])[F:38])[CH2:33][CH2:34]3)[C:26]([Cl:28])=[CH:27][C:20]=2[N:19]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 24614Phosphorus tribromideHCID 70297m-Chloroperbenzoic acidHCID 86674348N-(4-Trifluoromethyl-3-(5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)benzyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 60162278N-(4-Trifluoromethyl-3-(5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)benzyl)-2-methylpropane-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of N-(4-trifluoromethyl-3-(5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)benzyl)-2-methylpropane-2-sulfinamide (140 mg, 0.23 mmol), m-chloroperoxybenzoic acid (198 mg, 1.15 mmol) and CHCl3 (7 mL) was stirred at rt for 15 min. The mixture was poured into brine and extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was mixed with PBr3 (144 mg, 0.50 mmol) and DCM (5 ml) and the mixture was stirred at rt overnight. The mixture was poured into H2O and extracted with DCM. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography gave the title compound.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. stirringthe mixture was stirred at rt overnight
  6. extractionextracted with DCM
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by column chromatography

Sources & evidence

ORD record
ord-3293b8e68405419488e9f3935631bd3c
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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