Triethylamine → HCID 178519333, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-benzimidazole-5-carboxylic acid (4-6, 130 mg, 0.43 mmol, 1 equiv, tert-butyl l-piperazinecarboxylate (79 mg, 0.43 mmol, 1.0 equiv), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (97 mg, 0.51 mmol, 1.2 equiv), 1-hydroxy-7-azabenzotriazole (70 mg, 0.51 mmol, 1.2 equiv), and triethylamine (0.148 mL, 1.06 mmol, 2.50 equiv) in DMF (5.0 mL) was stirred at 23° C. for 20 h. The reaction mixture was partitioned between water (50 mL) ethyl actate (3×50 mL). The combined organic layers were dried over sodium sulfate and concentrated. A solution of the residue, DMSO (10 uL), and water (10 uL) in a 1:1 mixture of dichloromethane and trifluoroacetic acid (20 mL) was stirred at 23° C. for 45 min. The reaction mixture was concentrated, and the residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA present). The desired fractions were partitioned between saturated sodium bicarbonate solution (50 mL) and a 10% solution of methanol in dichloromethane (2×50 mL) to provide 3-[5-(1-piperazinylcarbonyl)-1H-benzimidazol-2-yl]-2(1H)-quinolinone (14-1) as its free base. 1H NMR (500 MHz, DMSO-d6) δ 11.83 (s, 1H), 8.59 (s, 1H), 7.74 (m, 2H), 7.53 (m, 2H), 7.39 (m, 2H), 7.26 (m, 2H), 3.61 (br m, 1H), 3.60 (br m, 1H), 3.32 (br m, 1H), 1.98 (br m, 1H), 1.89 (br m, 1H), 1.62 (br m, 2H).

Provenance & Evidence