Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine → HCID 67388898, compound

Participants

Reaction Steps

Sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (211 mg) and tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine (90 mg) were added to a stirred solution of 3-(1,3-benzoxazol-2-yl)-5-ethynyl-pyridin-2-amine (125 mg) in THF (15 ml) at room temperature. To the reaction mixture was then added water (5 ml), tert-butyl 4-azidopiperidine-1-carboxylate (180 mg) in THF (1 ml) and tetrakis(acetonitrile)copper(I) hexafluorophosphate (9.9 mg). The resulting solution was stirred overnight: a precipitate appeared. The precipitate was filtered, washed successively with water, THF, diethyl ether and petroleum ether, and dried under vacuum at 50° C. to afford tert-butyl 4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]triazol-1-yl]piperidine-1-carboxylate (218 mg) as a solid; NMR Spectrum: (DMSOd6) 1.44 (s, 9H), 1.82-1.96 (m, 2H), 2.07-2.21 (m, 2H), 3.01 (bs, 2H), 3.99-4.20 (m, 2H), 4.72-4.85 (m, 1H), 7.40-7.53 (m, 2H), 7.80-8.04 (m, 4H), 8.72 (s, 2H), 8.78 (s, 1H); Mass spectrum: M+H+: 462

Provenance & Evidence