Hydrochloric Acid → HCID 89813166, compound

Participants

Reaction Steps

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (80 mg, 0.27 mmol) and 4-amino-2,2-dimethyl-butyric acid methyl ester, trifluoroacetic acid salt (210 mg, 0.81 mmol) in 0.5 M NaOMe/MeOH solution (1.62 mL, 0.81 mmol) was microwaved at 130° C. for 3 h. The reaction mixture was diluted with water (50 mL), acidified by 1 N HCl to pH=3-4 and then extracted with EtOAc. Organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated. Residue was purified by silica gel chromatography, eluting with 5-50% EtOAc/hexanes, to provide the title compound 26 mg (0.063 mmol) in 23.6% yield. 1H NMR in CDCl3, δ ppm: 13.23 (s, 1H), 8.40 (s, 1H), 8.32 (d, J=8.8 Hz, 1H), 7.97 (br t, 1H), 7.42 (m, 4H), 7.12 (m, 3H), 3.64 (s, 3H), 3.52 (m, 2H), 1.95 (dd, J=9.1, 5.9 Hz, 2H), 1.27 (s, 6H).

Provenance & Evidence