Hydrochloric Acid → HCID 51349216, compound

Participants

Reaction Steps

To a solution of 1-(isoquinolin-6-yl)-2-phenylethanone (Intermediate 68) (100 mg, 0.4 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (85 mg, 0.4 mmol) and urea (72 mg, 1.2 mmol) in 2 mL of ethanol was added 0.5 mL of conc. HCl and the mixture was refluxed overnight. The reaction was evaporated and purified by preparative HPLC (20-50% acetonitrile+0.15% trifluoroacetic acid in water, over 15 min.), followed by column chromatography (PE: EtOAc=3:1˜EtOAc:MeOH=10:1) to give Compound 133 (67 mg, yield 34.3%). 1H NMR (CD3OD 400 MHz): δ 9.18 (s, 1H), 8.42 (d, J=5.6 Hz, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.94 (s, 1H), 7.76 (d, J=6.0 Hz, 1H), 7.65 (d, J=2.0 Hz, 1H), 7.48 (dd, J=2.0 Hz, 8.8 Hz, 1H), 7.17 (d, J=1.6 Hz, 1H), 7.07-7.06 (m, 3H), 6.95-6.93 (m, 2H), 5.45 (s, 1H), 4.13-4.02 (m, 2H), 1.41 (t, J=6.8 Hz, 3H); MS (ESI): m/z 483.3 [M+1]+.

Provenance & Evidence