Lithium Hydroxide → HCID 71062246, compound

Participants

Reaction Conditions

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)-2-naphthoate (Example 16, 84 mg, 0.10 mmol) in EtOH (0.5 mL) and THF (0.5 mL) was added 2N LiOH (0.5 mL, 1.03 mmol). The reaction mixture was stirred for 2 h at 40° C., concentrated to remove volatiles, diluted with water and quenched with 1N HCl. The solution was concentrated in vacuo and purified by preparative HPLC to afford the title compound (57 mg, 68%) as a white solid. 1H NMR (DMSO-d6, 2:1 mixture of amide rotamers) δ 8.41 (s, 1H), 8.36 (s, 1H), 8.07 (t, J=7.3 Hz, 2H), 7.99 (d, J=1.3 Hz, 1H), 7.88 (s, 2H), 7.79 (d, J=8.8 Hz, 1H), 7.55-7.51 (m, 1H), 7.20-7.07 (m, 3.5H), 6.97 (d, J=7.5 Hz, 0.5H), 4.10 (br s, 6H), 2.97 (br s, 1.5H), 2.74 (br s, 1.5H), 2.19 (s, 2H), 2.14 (s, 1H), 1.38 (br s, 1H), 1.29-1.12 (m, 6H), 1.01-0.91 (m, 2H), 0.88-0.82 (m, 3H), 0.68-0.61 (m, 3H); MS(ESI+) m/z 784.2 (M+H)+.

Provenance & Evidence