Lithium borohydride → HCID 70689990, 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, 23 mg, 0.031 mmol). THF (1.0 mL) and then 2M lithium borohydride solution in THF (0.078 mL, 0.16 mmol) were added. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with sat. aq. sodium bicarbonate solution and extracted with EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product. The residue was purified by preparative HPLC to give the title compound (7.3 mg, 34%). 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.65 (s, 1H), 8.12-7.91 (m, 6H), 7.63-7.57 (m, 2H), 7.50-6.99 (m, 9.5H), 6.91-6.89 (m, 0.5H), 4.65-4.32 (m, 4H), 3.44-3.15 (m, 2H), 2.88-2.49 (m, 4H), 1.39-0.86 (m, 4H), 0.55-0.49 (m, 3H); MS(ESI+) m/z 699.2 (M+H)+.

Provenance & Evidence