Hydrochloric Acid → Bcl-xL antagonist 2

Participants

Reaction Conditions

Reaction Steps

The title compound 2-(8-(Benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid (1) was prepared by following procedure: To a solution of methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate (1C) (180 mg, 4 mmol) in THF (4 mL) and MeOH (2 mL) was added 2N NaOH (2 mL). The reaction mixture was stirred at 50° C. for 4 hours and neutralized by slowly adding 5% aq. HCl. The precipitate was then filtered, dried, dissolved in DMSO/MeOH (1:1) and purified by column chromatography on silica gel to provide the desired product 2-(8-(Benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid (1): 1H NMR (300 MHz, DMSO-D6) δ ppm 7.99 (1H, d), 7.76 (1H, d), 7.69 (1H, dd), 7.52 (1H, s), 7.38 (4H, m), 4.91 (2H, s), 3.75 (2H, t), 3.05 (2H, t). MS (ESI(+)): m/z 437 (M+H).

Provenance & Evidence