Lithium Hydroxide → HCID 71062151, compound

Participants

Reaction Steps

To a solution of ethyl 7-(N-(4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoyl)sulfamoyl)-1-naphthoate (Example 9, 9.4 mg, 0.012 mmol) in EtOH (0.5 mL) and THF (0.5 mL) was added 2N LiOH (58 μL, 0.12 mmol). The reaction mixture was stirred at room temperature for 30 min and then at 40° C. for 2 h. The reaction mixture was quenched with 6N HCl, and then extracted with CHCl3 (4×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (9.0 mg, 94%). 1H NMR (CD3OD, 2:1 mixture of amide rotamers) δ 9.90 (s, 1H), 8.40 (d, J=7.3 Hz, 1H), 8.23 (d, J=8.4 Hz, 1H), 8.17 (d, J=1.1 Hz, 1H), 8.08 (dd, J=8.4, 1.8 Hz, 1H), 7.98 (t, J=2.2 Hz, 1H), 7.79-7.74 (m, 1H), 7.71-7.64 (m, 1H), 7.24-7.04 (m, 4.5H), 6.90-6.88 (m, 0.5H), 4.53 (br s, 2H), 3.58-3.39 (m, 4H), 3.13 (d, J=1.3 Hz, 1H), 3.05-2.94 (m, 1H), 2.82 (br s, 1H), 2.79-2.66 (m, 1H), 2.33 (s, 2H), 2.28 (s, 1H), 1.49-1.20 (m, 6H), 1.13-0.98 (m, 2H), 0.96-0.84 (m, 3H), 0.80-0.64 (m, 3H); MS(ESI−) m/z 782.5 (M−H)−.

Provenance & Evidence