Hydrochloric Acid → HCID 86639688, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL round-bottomed flask was charged with [2-(dimethylamino)ethyl]triphenylphosphonium bromide (1114 mg, 2.69 mmol) and THF (5 mL). The reaction was cooled to 0° C. under nitrogen. Butyllithium (1.08 ml, 2.69 mmol) was added slowly and the reaction was stirred for 50 minutes. A solution of 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (350 mg, 1.08 mmol) in THF (5 mL) was added and the reaction was stirred at ambient temperature for 1.5 hours. The reaction was partitioned between EtOAc and water. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on a silica gel column (10 to 20% methanol in EtOAc with NH4OH) to afford the title compound (250 mg, 51.3% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 10.85 (bs, 1H), 10.49 (bs, 1H), 8.03 (d, 1H), 7.78 (s, 1H), 7.63 (d, 2H), 7.45-7.33 (m, 3H), 6.82 (m, 3H), 6.45 (m, 1H), 5.37 (s, 2H), 3.85 (m, 2H), 2.77 (d, 6H), 2.30 (s, 3H). Mass spectrum (apci) m/z=381.1 (M+H-2HCl).

Provenance & Evidence