Triethylamine → HCID 178433632, compound

Participants

Reaction Steps

To a solution of 3-[2-(4-chlorophenyl)-3,5-dihydro-6-methyl-3-oxo-2H-pyrazolo[4,3-c]pyridin-7-yl]benzoic acid (65 mg, 0.171 mmol) in anhydrous N,N-dimethylacetamide (2 ml) was added pyrrolidine (15.7 ml, 0.188 mmol), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (48.0 mg, 0.188 mmol), then, dropwise, anhydrous triethylamine (52.5 ml, 0.376 mmol). The mixture was stirred under nitrogen at room temperature for 18 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 3-5% MeOH/CH2Cl2) to give 63.2 mg (85%) of the title compound as a yellow solid; mp 253-255° C.; 1H NMR (360 MHz, DMSO-d6) δ1.85 (4H, m), 2.29 (3H, s), 3.49 (4H, br q, J 6.9 Hz), 7.41 (2H, d, J 9.0 Hz), 7.55-7.59 (3H, m), 7.66 (1H, s), 8.12 (2H, d, J 9.0 Hz), 8.58 (1H, s), 12.49 (1H, br s); MS (ES+) m/z 433/435 [H]+. Anal. found: C, 63.85; H, 4.96; N, 12.33. C24H21ClN4O2.H2O requires: C, 63.93; H, 5.14; N, 12.42%.

Provenance & Evidence