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

HRID 1258721Notes

Reaction equation

HRID 1258721 reaction equation
[CH3:1][C:2]([S:5](Cl)=[O:6])([CH3:4])[CH3:3].[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][C:10]=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.O>C(Cl)Cl>[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:14][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])=[CH:11][C:10]=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

5

Reactant 3

HCID 962WaterHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 679580774-Chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine

Product 1

HCID 67960673N-(4-Chloro-3-(5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino)benzyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methylpropane-2-sulfinic acid chloride (83 mg, 0.59 mmol) in DCM (2 mL) was added dropwise to a solution of 4-chloro-3-[5-chloro-1-methyl-6-(4-trifluoromethyl-piperidin-1-yl)-1H-benzo[d]imidazol-2-ylamino]benzylamine (265 mg, 0.56 mmol), TEA (113 mg, 1.12 mmol) and DCM (3 mL) at 0° C. under Ar. The mixture was stirred at rt overnight, poured into H2O and extracted with DCM. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Crystallization from DCM/PE gave the sub-title compound.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrystallization from DCM/PE

Sources & evidence

ORD record
ord-9d954e90449448b1972bba45a32186f6
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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