Potassium hydroxy sulfite → 1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carboxylic acid

HRID 1435492Notes

Reaction equation

HRID 1435492 reaction equation
[OH:1]OS([O-])=O.[K+].[C:7]([C:11]1[N:15]([CH2:16][CH:17]2[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19][CH2:18]2)[C:14]2[CH:25]=[CH:26][C:27]([S:29]([N:32]3[CH:36]=[C:35]([CH:37]=[O:38])[CH:34]=[N:33]3)(=[O:31])=[O:30])=[CH:28][C:13]=2[N:12]=1)([CH3:10])([CH3:9])[CH3:8]>CN(C=O)C>[C:7]([C:11]1[N:15]([CH2:16][CH:17]2[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19][CH2:18]2)[C:14]2[CH:25]=[CH:26][C:27]([S:29]([N:32]3[CH:36]=[C:35]([C:37]([OH:1])=[O:38])[CH:34]=[N:33]3)(=[O:31])=[O:30])=[CH:28][C:13]=2[N:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 579372961-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 579372991-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxone® (0.60 g, 0.97 mmol) was added to a solution of 1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carbaldehyde (0.41 g, 0.88 mmol) in DMF (15 mL). The reaction mixture was stirred overnight at ambient temperature and the solvent was concentrated. The product was recovered in DCM, washed with 10% HCl solution, brine and dried over anhydrous Na2SO4, The solvent was concentrated to provide the pure title compound as white solid. Yield: 0.38 g (89%); 1H NMR (400 MHz, CDCl3) δ 1.42-1.53 (m, 2 H), 1.56 (s, 9 H), 1.59-1.75 (m, 4 H), 2.02-2.20 (m, 3 H), 4.25 (d, J=7.42 Hz, 2 H), 7.46 (d, J=8.59 Hz, 1 H), 7.99 (dd, J=8.69, 1.86 Hz, 1 H), 8.01-8.08 (m, 2 H), 8.47 (d, J=1.56 Hz, 1 H), 8.68 (d, J=0.59 Hz, 1 H); MS (ESI) (M+H)+=481.0.

Workup

  1. concentrationthe solvent was concentrated
  2. customThe product was recovered in DCM
  3. washwashed with 10% HCl solution, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-48022814ebd847d2957bc8831d51a0bb
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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