Triethylamine → HCID 24784185, compound

Participants

Reaction Steps

To a solution of 8-[2-(4-amino-1-piperidinyl)ethyl]-2H-chromen-2-one hydrochloride (41 mg, 0.15 mmol), Et3N (0.10 mL), in 10% methanol/CH2Cl2 (5 mL) was added 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxaldehyde (32 mg, 0.17 mmol). The solution was allowed to stir at RT for 16 h, then sodium borohydride (7 mg, 0.17 mmol) was added. The solution was stirred for an additional 30 min then was concentrated under reduced pressure. Flash chromatography on silica gel (90:9:1 CHCl3/MeOH/conc NH4OH) gave the title compound (34 mg, 51%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.99 (d, J=9.6 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.32 (m, 1H), 7.11 (d, J=7.8 Hz, 1H), 6.47 (d, J=9.6 Hz, 1H), 4.17 (s, 2H), 3.57 (s, 2H), 3.36-3.04 (m, 5H), 3.00-2.84 (m, 2H), 2.62-2.38 (m, 2H), 2.33-2.10 (m, 2H), 1.87-1.62 (m, 2H); MS (ES) m/e 451.1 (M+H)+.

Provenance & Evidence