Sodium Hydroxide → HCID 68313427, compound

Participants

Reaction Steps

An orange solution of Example 54C (77 mg, 0.368 mmol), DMF (0.8 mL), i-Pr2NEt (0.135 mL, 0.773 mmol), and methyl 4-((2,5-dioxopyrrolidin-1-yloxy)carbonylamino)-1H-indazole-1-carboxylate (128 mg, 0.386 mmol) was stirred at ambient temperature. After 15 minutes, MeOH (1.60 mL) and sodium hydroxide (50 wt % in water, 0.058 mL, 1.1 mmol) were added. After 20 minutes of stirring, the mixture was diluted with EtOAc (30 mL) and washed with water (10 mL) and brine (10 mL), dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (75-100% EtOAc/hexanes, gradient elution) to provide the title compound (117 mg, 0.318 mmol, 86% yield). 1H NMR (400 MHz, DMSO-d6) δ 13.01 (s, 1H), 8.72 (s, 1H), 8.03 (s, 1H), 7.58 (d, J=7.3 Hz, 1H), 7.47-7.30 (m, 4H), 7.30-7.14 (m, 2H), 7.07 (d, J=8.3 Hz, 1H), 6.48 (d, J=6.1 Hz, 1H), 4.30 (s, 1H), 3.54 (d, J=6.6 Hz, 1H), 2.64-2.50 (m, 3H), 1.81 (d, J=13.8 Hz, 1H). MS (DCI) M/Z 369 [M+H]+.

Provenance & Evidence