Diisopropylethylamine → HCID 71136787, compound

Participants

Reaction Steps

5-[2-(Aminomethyl)-3-methylcyclopropyl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (35-2, 35 mg, 0.11 mmol, 1.0 equiv), isoxazole-3-carboxylic acid (2-6, 14.3 mg, 0.12 mmol, 1.5 equiv), DIPEA (0.040 mL, 0.23 mmol, 2.0 equiv) and HATU (48.4 mg, 0.12 mmol, 1.1 equiv) were added to anhydrous acetonitrile (1 mL). After stirring for 10 min at room temperature, LCMS showed consumption of starting material. Purification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O) provided 35-3 as a white solid. MS m/z (M+H): calculated=398.2188; observed=398.2195. 1H NMR δ (ppm)(CHCl3-d): 8.47 (1H, d, J=1.68 Hz), 7.04 (1H, d, J=7.90 Hz), 6.96 (1H, s), 6.83 (1H, d, J=1.67 Hz), 6.81 (1H, d, J=7.90 Hz), 3.76-3.65 (1H, m), 3.61 (2H, s), 3.60-3.52 (1H, m), 3.43 (3H, s), 1.82 (1H, dd, J=7.68, 3.43 Hz), 1.70-1.65 (1H, m), 1.64 (1H, dd, J=7.82, 0.02 Hz), 1.30 (3H, d, J=6.23 Hz), 1.02 (9H, s).

Provenance & Evidence