(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine → HCID 89455636, compound

HRID 1428788Notes

Reaction equation

[F:1][C:2]1[CH:20]=[C:19]([NH:21][C:22]([O:24]C2C=CC=CC=2)=O)[CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][S:6]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH2+:14])=[O:11])(=[O:8])=[O:7].[C:31]1([CH3:49])[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[C:42]([CH2:43][NH2:44])=[CH:41][CH:40]=[C:39]([C:45]([F:48])([F:47])[F:46])[N:38]=2)[CH:32]=1>C(#N)C.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:20]=[C:19]([NH:21][C:22]([NH:44][CH2:43][C:42]2[C:37]([C:33]3[CH:32]=[C:31]([CH3:49])[CH:36]=[CH:35][CH:34]=3)=[N:38][C:39]([C:45]([F:48])([F:46])[F:47])=[CH:40][CH:41]=2)=[O:24])[CH:18]=[CH:17][C:3]=1[CH2:4][NH:5][S:6]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:7])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

2-(N-(2-Fluoro-4-(phenoxycarbonylamino)benzyl)sulfamoylcarbamoyloxy)-2-methylpropan-1-ylium (100 mg, 0.225 mmol) was dissolved in acetonitrile. (2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (60 mg, 0.225 mmol) and 4-dimethylaminopyridine (27 mg) were added to the solution. The reaction mixture was stirred for overnight at 50° C. The mixture was extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave tert-butyl N-(2-fluoro-4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)sulfamoylcarbamate (70 mg, 51%).

Workup

extractionThe mixture was extracted with ethyl acetate
washwashed with brine
dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record: ord-4a930dd291f7404a9a9cf9f2722421a6
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937092B2

Reaction notes

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