Ethanolamine → N-(2-Hydroxy-ethyl)-6-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-nicotinamide

To a mixture of 6-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid (200 mg, 0.65 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (228 mg, 0.71 mmol) was added DMF (2 mL). After stirring for 2 min at ambient temperature N,N-diisopropyl ethyl amine (553 μL, 3.23 mmol) and ethanolamine (47 μl, 0.78 mmol) were added and the resulting solution was stirred for 2 h at this temperature. It was diluted with ethyl acetate (15 mL) and washed with water (20 mL) and brine (15 mL). The aqueous layers were extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate: methanol=30:70:0 to 0:95:5) afforded the title compound (200 mg, 88%) as a white solid. MS: m/e=353.2 [M+H]+.

1. additionwere added
2. washwashed with water (20 mL) and brine (15 mL)
3. extractionThe aqueous layers were extracted with ethyl acetate
4. dry with materialthe combined organic layers were dried over sodium sulfate
5. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate: methanol=30:70:0 to 0:95:5)

ORDレコード

ord-cebde54c669142419d9a5dc7e4fc39a9

出典データセット

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08877783B2