Sodium Hydroxide → HCID 70681580, compound

Participants

Reaction Steps

A 25 mL round bottom flask was charged with ethyl 5-butyl-4-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1-phenyl-1H-pyrazole-3-carboxylate (Example 223, 52 mg, 0.070 mmol). THF (2.0 mL) and then 1N aq. NaOH solution (0.140 mL, 0.140 mmol) were added. The reaction mixture was stirred at room temperature overnight. After concentration in vacuo to remove the THF, the reaction mixture was made acidic (pH 3-4) with conc. HCl. The product was extracted with EtOAc and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product (50 mg, 100%) as a yellow oil. A portion (approx. 10 mg) was purified by preparative HPLC to give the title compound (4 mg). 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.63 (s, 1H), 8.11-8.05 (m, 3H), 8.01-7.98 (m, 1H), 7.94 (d, J=4 Hz, 1H), 7.90 (d, J=4 Hz, 1H), 7.61-7.55 (m, 2H), 7.52-7.35 (m, 6H), 7.19-7.04 (m, 3.5H), 6.86-6.82 (m, 0.5H), 4.90-4.80 (m, 0.5H), 4.51-4.36 (m, 1.5H), 3.65-3.43 (m, 2H), 2.88-2.49 (m, 4H), 1.12-0.89 (m, 4H), 0.61-0.56 (m, 3H); MS (ESI+) m/z 713.3 (M+H)+.

Provenance & Evidence