Sodium Hydroxide → HCID 68313584, compound

Participants

Reaction Steps

An orange solution of Example 55C (20 mg, 0.115 mmol), DMF (1 mL), DIPEA (0.042 mL, 0.242 mmol), and methyl 4-((2,5-dioxopyrrolidin-1-yloxy)carbonylamino)-1H-indazole-1-carboxylate (40.3 mg, 0.121 mmol) was stirred at ambient temperature. After 15 minutes, MeOH (2.00 mL) and sodium hydroxide (50 wt % in water, 0.018 mL, 0.346 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 (27.5 mg, 0.083 mmol, 71.7% yield). 1H NMR (400 MHz, DMSO-d6) δ 13.0 (brs, 1H), 8.63 (s, 1H), 8.09 (d, J=1.0 Hz, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.39-7.33 (m, 2H), 7.30 (t, J=7.5 Hz, 2H), 7.24-7.16 (m, 2H), 7.05 (d, J=8.2 Hz, 1H), 6.52 (d, J=7.6 Hz, 1H), 4.49-4.38 (m, 1H), 3.50-3.41 (m, 1H), 2.24 (dt, J=12.7, 7.6 Hz, 1H), 1.66-1.58 (m, 2H), 1.29-0.90 (m, 1H), 0.69 (q, J=4.2 Hz, 1H), 0.48 (td, J=7.7, 5.2 Hz, 1H). MS (DCI) M/Z 350 [M+NH4]+.

Provenance & Evidence