Phenyl 3-fluoro-4-(methylsulfonamidomethyl)phenylcarbamate → N-(2-Fluoro-4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

HRID 1428741Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:23])OC2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=[C:32]([C:38]([F:41])([F:40])[F:39])[N:31]=2)[CH:25]=1>C(#N)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]([NH:37][CH2:36][C:35]2[C:30]([C:26]3[CH:25]=[C:24]([CH3:42])[CH:29]=[CH:28][CH:27]=3)=[N:31][C:32]([C:38]([F:41])([F:39])[F:40])=[CH:33][CH:34]=2)=[O:23])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of phenyl 3-fluoro-4-(methylsulfonamidomethyl)-phenylcarbamate (67 mg, 0.198 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (53 mg, 0.198 mmol) in acetonitrile were added 4-dimethylaminopyridine (24 mg, 0.198 mmol). The reaction mixture was stirred for 15 h at 50° C. The mixture was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. N-(2-Fluoro-4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 27) (72 mg) was obtained as 72% yield.

Workup

washwashed with water and brine
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customThe filtrate removed in vacuo
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-c85e12543eaf490da142f71af7409c9c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937092B2

Reaction notes

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