Methanol → HCID 71555554, compound

Participants

Reaction Conditions

Reaction Steps

The product of Step D (0.72 g, 1.45 mmol) was dissolved in methanol (4 mL, 100 mmol) and tetrahydrofuran (4 mL, 50 mmol). To the resulting solution was added hydrazine (2 mL, 60 mmol). The solution was stirred at 50° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by combi-flash chromatography eluting with MeOH/EtOAc (20-60%). The product was further purified by prep.-LC/MS (pH=10). The purification afforded 345 mg (37.3% yield) of the final product as white solid. LC-MS found: 365.2 (M+1)+; 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.70 (d, J=3.6 Hz, 1H), 7.66 (s, 1H), 7.58 (dd, J1=7.8 Hz, J2=1.2 Hz, 1H), 7.48 (d, J=1.8 Hz, 1H), 7.23 (dd, J1=7.8 Hz, J2=6.3 Hz, 1H), 7.03 (m, 2H), 6.93 (ddd, J1=8.7 Hz, J2=8.4 Hz, J3=2.4 Hz, 1H), 6.45 (d, J=2.1 Hz, 1H), 4.46 (s, 2H), 4.40 (m, 1H), 3.86 (s, 3H), 3.04 (dd, J1=14.4 Hz, J2=5.1 Hz, 1H), 2.88 (dd, J1=14.40 Hz, J2=4.5 Hz, 1H), 2.82 (d, J=6.9 Hz, 2H).

Provenance & Evidence