Dimethylformamide → HCID 71767519, compound

Participants

Reaction Steps

Oxalyl chloride (229 mg, 1.80 mmol, 1.5 eq) was added to a solution of 4-(dimethylamino)-1-ylbut-2-enoicacid hydrochloride (200 mg, 1.2 mmol, 1.0 eq) in THF (4 mL) under ice-water bath. This was followed by the addition of a trace amount of DMF. This solution was stirred at rt for 3 hours before added to a solution of. This solution was then cooled in an ice-water bath, and 6-amino-4-((4-phenoxyphenyl)amino)quinoline-3-carbonitrile (253 mg, 0.72 mmol, 0.6 eq) in N-methylpyrrolidinone (5 mL) was added dropwise. The reaction was allowed warmed to room temperature over 4 hours before poured into saturated aqueous NaHCO3 solution, extracted with EA (3×50 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by flash column chromatography in silica gel to give (E)-N-(3-cyano-4-((4-phenoxyphenyl)amino)quinolin-6-yl)-4-(dimethylamino)but-2-enamide (Compound 21) as an off-white solid 39 mg. 1H-NMR (300 MHz, DMSO-d6): δ 8.83 p.p.m. (1H, s), 8.56 (1H, s), 7.97 (1H, d, J=6.6 Hz), 7.85 (1H, m), 7.52 (1H, dd, J=6.6, 1.5 Hz), 7.35 (2H, m), 7.12 (1H, m), 7.07 (5H, m), 7.02 (2H, m), 6.22 (1H, d, J=11.7 Hz), 3.19 (3H, m), 2.38 (6H, s).

Provenance & Evidence