Hydrochloric Acid → HCID 86690753, compound

Participants

Reaction Steps

To 2-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde (10 mg, 0.02 mmol, 1 equiv) suspended in EtOH (1 mL) was added HCl (0.1 mL, 3 N). The solution turned homogeneous and the mixture was stirred at rt overnight. The EtOH was partially removed by blowing in N2 gas and basified to pH 9. The aqueous solution was extracted with EtOAc three times. The organic layer was dried over Na2SO4 and concentrated. The crude was purified on silica gel using MeOH and DCM as eluent to give 5-((3-(1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (6.0 mg, 83%) as a white solid. NMR (400 MHz; CDCl3) δ=10.17 (s, 1H), 9.25 (s, 1H), 8.18 (s, 1H), 8.05 (d, 1H), 7.99 (d, 1H), 7.73 (t, 1H), 7.60-7.68 (m, 2H), 7.03 (s, 1H), 6.70 (d, 1H), 5.85 (s, 2H), 3.85 (s, 3H). LRMS (M+H+) m/z 361.1.

Provenance & Evidence