4-(2,2-dimethylpropyl)-N,N-dimethyl-2-{[4-(1H-pyrazol-1-yl)phenyl]acetyl}-1H-imidazole-1-sulfonamide → 4-(2,2-dimethylpropyl)-2-{1-hydroxy-1-methyl-2-[4-(1H-pyrazol-1-yl)phenyl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 425368Notes

Reaction equation

[CH3:1][Li].[CH3:3][C:4]([CH3:32])([CH3:31])[CH2:5][C:6]1[N:7]=[C:8]([C:17](=[O:30])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)=[CH:21][CH:20]=2)[N:9]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH:10]=1>O1CCCC1>[CH3:3][C:4]([CH3:32])([CH3:31])[CH2:5][C:6]1[N:7]=[C:8]([C:17]([OH:30])([CH3:1])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)=[CH:21][CH:20]=2)[N:9]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:12])=[O:13])[CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Methyllithium (1.6 M in diethyl ether) (0.327 mL, 0.524 mmol) was added to a −78° C. solution of 4-(2,2-dimethylpropyl)-N,N-dimethyl-2-{[4-(1H-pyrazol-1-yl)phenyl]acetyl}-1H-imidazole-1-sulfonamide (75 mg, 0.175 mmol) in tetrahydrofuran (2 mL). After stirring at −78° C. for 30 min, the reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% EtOAc/hexane afforded 4-(2,2-dimethylpropyl)-2-{1-hydroxy-1-methyl-2-[4-(1H-pyrazol-1-yl)phen yl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

customthe reaction mixture was quenched with saturated aqueous ammonium chloride
extractionextracted with methylene chloride
dry with materialThe combined organic extracts were dried (sodium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a99f590ef23f4ecf8e3b89f02ad58e49
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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