m-Chloroperbenzoic acid → HCID 67960675, compound

HRID 1258722Notes

Reaction equation

HRID 1258722 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][S:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[CH:4][C:3]=1[NH:16][C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[C:24]([N:28]3[CH2:33][CH2:32][CH:31]([C:34]([F:37])([F:36])[F:35])[CH2:30][CH2:29]3)[C:25]([Cl:27])=[CH:26][C:19]=2[N:18]=1.ClC1C=C(C=CC=1)C(OO)=[O:43]>C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][NH:7][S:8]([C:10]([CH3:11])([CH3:13])[CH3:12])(=[O:43])=[O:9])=[CH:4][C:3]=1[NH:16][C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[C:24]([N:28]3[CH2:29][CH2:30][CH:31]([C:34]([F:36])([F:35])[F:37])[CH2:32][CH2:33]3)[C:25]([Cl:27])=[CH:26][C:19]=2[N:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 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

Product 1

HCID 67960675HCID 67960675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 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 (298 mg, 0.52 mmol), m-chloroperoxybenzoic acid (127 mg, 0.74 mmol) and DCM (20 mL) was stirred at rt overnight. The mixture was basicified to pH ˜8-9 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. Crystallization from DCM/Et2O gave the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCrystallization from DCM/Et2O

Sources & evidence

ORD record
ord-3c3c5afb55b84c33b6f2a45aebd6ee6e
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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