HCID 59140396, compound → 2-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 216417Notes

Reaction equation

C([Li])CCC.[CH3:6][C:7]([CH3:21])([CH3:20])[CH2:8][C:9]1[N:10]=[CH:11][N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=1.[F:22][C:23]([F:43])([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)=[CH:32][CH:31]=1)[C:24](N(OC)C)=[O:25]>O1CCCC1>[F:43][C:23]([F:22])([C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)=[CH:34][CH:35]=1)[C:24]([C:11]1[N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=[C:9]([CH2:8][C:7]([CH3:21])([CH3:20])[CH3:6])[N:10]=1)=[O:25]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (1.6 M in hexane) (0.60 mL, 0.96 mmol) was added to a −78° C. solution of 4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (234 mg, 0.96 mmol) in tetrahydrofuran (10 mL). After stirring at −78° C. for 10 min, 2,2-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-N-methoxy-N-methylacetamide (296 mg, 0.96 mmol) was added and the reaction allowed to warm to ambient temperature, quenched with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 2-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

temperatureto warm to ambient temperature
customquenched with water
extractionextracted with methylene chloride and ethyl acetate
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7139a5e741384d0588d9fce309b0ead5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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