Diisopropylethylamine → 1-(2,2-Dimethylpropyl)-5-[2-(isoxazol-3-ylcarbonyl)-1,2,3,3a,4,6a-hexahydro-cyclopenta-[c]pyrrol-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

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Reaction Steps

1-(2,2-Dimethylpropyl)-5-(1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (8-4, 100 mg, 0.30 mmol, 1.0 equiv), isoxazole-3-carboxylic acid (2-6, 52 mg, 0.46 mmol, 1.5 equiv), DIPEA (0.16 mL, 0.91 mmol, 3.0 equiv) and HATU (175 mg, 0.46 mmol, 1.5 equiv) were added to anhydrous acetonitrile (3 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 8-5 as a white solid. MS m/z (M+H): calculated=422.2188; observed=422.2201. 1H NMR δ (ppm)(CHCl3-d): 8.42 (1H, dd, J=7.77, 1.64 Hz), 7.12 (1H, dd, J=8.03, 1.54 Hz), 7.01 (1H, dd, J=8.02, 4.63 Hz), 6.76 (1H, d, J=1.64 Hz), 6.43 (1H, d, J=13.40 Hz), 4.32 (1H, dd, J=12.00, 8.94 Hz), 4.19 (1H, dd, J=12.14, 2.21 Hz), 4.15-4.08 (1H, m), 4.08 (1H, t, J=8.61 Hz), 4.01-3.85 (1H, m), 3.64 (2H, s), 3.49 (3H, d, J=2.90 Hz), 3.22-3.05 (1H, m), 3.06-2.98 (1H, m), 2.85-2.70 (1H, m), 1.02 (9H, s).

Provenance & Evidence