Dimethylformamide → HCID 66880231, compound

HRID 2094411Notes

Reaction equation

F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl.CN.[CH3:30][N:31](C=O)C>O>[CH3:30][NH:31][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.55 g of potassium carbonate, 0.14 g of methylamine hydrochloride, and 3 ml of DMF was stirred while heating at 60° C. for three hours. To the mixture, 0.55 g of potassium carbonate and 0.14 g of methylamine hydrochloride were added, and the reaction mixture was stirred while heating for further two hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and resultant crystals were washed with diethyl ether to give 0.13 g of methyl-[4-(5-trifluoromethylbenzoxazole-2-yl)pyridin-3-yl]amine (hereinafter, referred to as “active compound 83”).

Workup

stirringthe reaction mixture was stirred
temperaturewhile heating for further two hours
extractionfollowed by extraction with ethyl acetate twice
washThe combined organic layers were washed with a saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
washresultant crystals were washed with diethyl ether

Sources & evidence

ORD record: ord-565216527a3a4bd8862cf800ff77eb78
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445522B2

Reaction notes

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