Triethylamine → N-[2-amino-4-(6-cyano-1H-indazol-1-yl)pyrimidin-5-yl]-3-methyloxetane-3-carboxamide

Participants

Reaction Steps

To a mixture of 3-methyloxetane-3-carboxylic acid (17 mg, 0.143 mmol) and HATU (54.5 mg, 0.143 mmol) was added a solution of 1-(2,5-diaminopyrimidin-4-yl)-1H-indazole-6-carbonitrile (30 mg, 0.072 mmol) in DMF (0.5 mL) followed by triethylamine (0.030 mL, 0.215 mmol). The mixture was stirred at RT for 10 min, then diluted with EtOAc (10 mL) and washed with water (2×3 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the crude compound. The crude product was purified by flash chromatography (Isolute column, 90% EtOAc in heptane to 100% EtOAc and then 0.5% MeOH/EtOAc) to afford the title compound as a pale yellow solid: 1H NMR (250 MHz, DMSO) δ 1.61 (3H, s), 4.31 (2H, d, J=5.94 Hz), 4.83 (2H, d, J=5.94 Hz), 7.20 (2H, br. s.), 7.65-7.92 (1H, m), 8.12 (1H, dd, J=8.22, 0.76 Hz), 8.49 (1H, s), 8.64 (1H, d, J=0.91 Hz), 9.14 (1H, s), 9.70 (1H, s); LC-MS: m/z=+350.1 (M+H)+.

Provenance & Evidence