Potassium hydroxy sulfite → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid

HRID 1435446Notes

Reaction equation

HRID 1435446 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]=[CH:33][C:32]([CH:35]=[O:36])=[CH: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]=[CH:33][C:32]([C:35]([OH:1])=[O:36])=[CH: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 23707502Potassium hydroxy sulfiteHCID 579373391-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehyde

Product 1

HCID 579373191-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxone (784 mg, 1.28 mmol) was added to a solution of 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehyde (366 mg, 0.85 mmol) in DMF (15 mL). The reaction mixture was stirred overnight at room temperature and used directly for step A. MS (ESI) (M+H)+=445.88

Sources & evidence

ORD record
ord-a94470ae470e43f69bae0c6c667423c1
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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