Hydrochloric Acid → HCID 86639686, compound

Participants

Reaction Steps

A 20 mL vial was charged with 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (100 mg, 0.31 mmol) and THF (3 mL). morpholine (0.032 ml, 0.37 mmol) was added and the reaction was stirred for 10 minutes. NaBH(OAc)3 (326 mg, 1.54 mmol) was added and the reaction was stirred for 30 minutes. The reaction was poured into saturated sodium bicarbonate and extracted with EtOAc. The organic layer was washed with water and brine and then dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (0 to 10% methanol in EtOAc containing ammonia) to afford the title compound (101.7 mg, 70.49% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 11.77 (bs, 1H), 11.05 (bs, 1H), 8.08 (m, 2H), 7.64 (d, 2H), 7.45-7.32 (m, 3H), 6.83 (s, 1H), 5.35 (s, 2H), 4.32 (d, 2H), 3.87 (m, 4H), 3.20 (d, 2H), 3.03 (m, 2H), 2.31 (s, 3H). Mass spectrum (apci) m/z=397.1 (M+H-2HCl).

Provenance & Evidence