Methanol → 4-[6-Amino-5-(5-chloro-8-methoxyisoquinolin-3-yl)-pyridin-3-yl]benzoic acid

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Reaction Conditions

Reaction Steps

To a solution of methyl 4-[6-amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-benzoate (0.13 g, 0.32 mmol) in methanol (5 mL) and water (0.5 mL) was added NaOH (0.24 g, 6 mmol), and the mixture was heated at 50° C. for 16 h. The solvents were evaporated at reduced pressure, and the residue was neutralized with acetic acid. The solid formed was filtered off and dried in vacuo to give the title compound. 1H NMR (400 MHz, DMSO-d6): δ=12.82 (very brs, 1H), 9.63 (s, 1H), 8.51 (d, J=2.4 Hz, 1H), 8.35 (s, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.03-7.98 & 7.90-7.85 (AA′BB′, 4H), 7.92 (d, J=8.0 Hz, 1H), 7.27 (brs, 2H), 7.15 (d, J=8.0 Hz, 1H), 4.07 (s, 3H). MS(ES+): m/z=406.08/408.03 (100/53) [MH+]. HPLC: tR=3.00 min (polar—5 min, ZQ3).

Provenance & Evidence