Propylamine → HCID 178457735, compound

Participants

Reaction Steps

To a solution of 3,5-dihydro-3-oxo-2-phenyl-2H-pyrazolo[4,3-c]pyridine-7-carboxylic acid (50 mg, 0.196 mmol) in anhydrous N,N-dimethylacetamide (2 ml) was added propylamine (17.8 ml, 0.216 mmol), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (55 mg, 0.216 mmol), then, dropwise, anhydrous triethylamine (60 ml, 0.430 mmol). The mixture was stirred under nitrogen at room temperature for 2 h. Water (5 ml) was then added and the mixture was stirred before collecting the solid by filtration. The solid was washed with water, then hexane, and dried under vacuum at 70° C. The solid was then purified by recrystallisation (CH2Cl2-MeOH-EtOAc) to afford 39.1 mg (67%) of the title compound as an orange solid; 1H NMR (360 MHz, DMSO-d6) δ0.99 (3H, t, J 7.3 Hz), 1.62 (2H, sextet, J 7.2 Hz), 3.41 (2H, q, J 6.8 Hz), 7.21 (1H, t, J 7.4 Hz), 7.47 (2H, t, J 7.5 Hz), 8.16 (1H, s), 8.18 (2H, d, J 7.6 Hz), 8.68 (1H, s), 8.70 (1H, t), 12.69 (1H, br s); MS (ES+) m/z 297 [MH]+.

Provenance & Evidence