1,1'-Carbonyldiimidazole → HCID 71062260, compound

Participants

Reaction Steps

To a solution of 2-(4-chloro-3-(dibutylcarbamoyl)-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazol-5-yl)acetic acid (Example 171, 24 mg, 0.031 mmol) in THF (625 μL) was added CDI (16 mg, 0.10 mmol). The resulting solution was heated at reflux for 30 min and then cooled to room temperature. Cyclopropanesulfonamide (14 mg, 0.12 mmol) was then added followed by DBU (24 μL, 0.16 mmol), and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was then diluted with EtOAc, washed with 1N aq. HCl solution (2×) and extracted with EtOAc (3×). The combined organic extracts were washed with sat. aq. NaCl solution, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (5 mg, 16%) as a white solid after lyophilization. 1H NMR (CD3OD, 2:1 mixture of amide rotamers) δ 8.74 (s, 1H), 8.16-7.96 (m, 6H), 7.81-7.64 (m, 3H), 7.28-7.05 (m, 3.5H), 6.91 (d, J=7.5 Hz, 0.5H), 4.71-4.33 (m, 1.5H), 4.12-2.55 (m, 11.5H), 1.53-0.84 (m, 15H), 0.76 (t, J=7.4 Hz, 2H), 0.67 (t, J=7.4 Hz, 1H); MS(ESI+) m/z 887.5 (M+H)+.

Provenance & Evidence