Sodium borohydride → HCID 11662684, compound

Participants

Reaction Steps

To a stirred solution of [((3S)-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amine (0.22 g, 0.77 mmole) in dry CH2Cl2 (25 mL) and dry EtOH (10 mL) at RT was added 3-oxo-3,4-dihydro-2H-pyrido[1,4]thiazine-6-carboxaldehyde (0.15 g, 0.77 mmole). After 24 h, at RT was added NaBH4 (0.03 g, 0.85 mmole). After 24 h, silica gel (5 g) was added to the reaction solution and the suspension was concentrated under vacuum to a dry solid. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.25 g, 70%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 8.78 (d, J=4.5 Hz, 1H), 18.29 (d, J=9.1 Hz, 1H), 7.85 (m, 2H), 7.36 (d, J=9.1 Hz, 1H), 7.15 (d, J=5.8 Hz, 1H), 4.38 (s, 2H), 4.19 (s, 3H), 3.91 (m, 2H), 3.82 (m, 4H), 3.67 (s, 2H), 3.31 (m, 2H), 3.18 (m, 1H), 2.55 (m, 2H), 2.10 (m, 2H). LC-MS (ES) m/e 465 (M+H)+.

Provenance & Evidence