HCID 23659910, compound → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acid

HRID 1435479Notes

Reaction equation

HRID 1435479 reaction equation
[OH:1]OS([O-])=O.[K+].[C:7]([C:11]1[N:15]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:14]2[CH:23]=[CH:24][C:25]([S:27]([N:30]3[CH:34]=[C:33]([CH:35]=[O:36])[CH:32]=[N:31]3)(=[O:29])=[O:28])=[CH:26][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][O:20][CH2:19][CH2:18]2)[C:14]2[CH:23]=[CH:24][C:25]([S:27]([N:30]3[CH:34]=[C:33]([C:35]([OH:1])=[O:36])[CH:32]=[N:31]3)(=[O:29])=[O:28])=[CH:26][C:13]=2[N:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 23659910HCID 23659910, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 579372951-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxone (596 mg, 0.97 mmol) was added to a solution of 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrazole-4-carbaldehyde (380 mg, 0.88 mmol) (see example 23 for preparation) in DMF (15 mL). The resulting mixture was stirred overnight at room temperature and the solvent was concentrated. The residue was dissolved in DCM, washed with 10% HCl solution and dried over anhydrous Na2SO4. The solvent was concentrated to provide the title compound as white solid Yield: 330 mg (74%); MS (ESI) (M+H)+=447.09.

Workup

  1. concentrationthe solvent was concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with 10% HCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-985d1f1598ad4725a9a235c5721ea39b
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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