m-Chloroperbenzoic acid → HCID 46908740, compound

HRID 1410249Notes

Reaction equation

HRID 1410249 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:36]([O:37][CH2:38][CH:39]([F:41])[F:40])=[CH:35][C:14]3[N:15]([CH3:34])[C:16]([NH:18][C:19]4[CH:24]=[C:23]([CH2:25][NH:26][S:27]([C:29]([CH3:32])([CH3:31])[CH3:30])=[O:28])[CH:22]=[CH:21][C:20]=4[Cl:33])=[N:17][C:13]=3[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:47]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:36]([O:37][CH2:38][CH:39]([F:41])[F:40])=[CH:35][C:14]3[N:15]([CH3:34])[C:16]([NH:18][C:19]4[CH:24]=[C:23]([CH2:25][NH:26][S:27]([C:29]([CH3:31])([CH3:32])[CH3:30])(=[O:47])=[O:28])[CH:22]=[CH:21][C:20]=4[Cl:33])=[N:17][C:13]=3[CH:12]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 46908739HCID 46908739, compound

Product 1

HCID 46908740HCID 46908740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-bromo-phenyl)-2-(2-chloro-5-{[(tert-butylsulfinyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide (100 mg; 0.15 mmol), m-chloroperoxybenzoic acid (28 mg; 0.16 mmol) and DCM (20 mL) was stirred over night at rt. The mixture was basicified to pH ˜8-9 and extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give the title compound. Yield: 24 mg (23%). 200 MHz 1H-NMR (DMSO-d6, ppm) 10.06-10.02 (1H, m) 7.75-7.62 (4H, m) 7.54-7.44 (4H, m) 7.27-7.17 (2H, m) 6.95-6.84 (1H, m) 6.57-6.49 (1H, m) 4.58-4.42 (2H, m) 4.16-4.09 (2H, m) 3.57-3.51 (3H, m) 1.29 (9H, s). MS m/z: 684, 686, 690 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2f39dbbe42654e55994faa41a4cea589
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

Loading…