1-Hydroxybenzotriazole → HCID 71208829, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamoyl)benzoic acid (25.3 mg, 0.058 mmol), 1-amino-2-methylpropan-2-ol (5.21 mg, 0.058 mmol), 1-hydroxybenzotriazole (HOBT) (12.9 mg, 0.094 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (18.1 mg, 0.094 mmol) in methylene chloride at 25° C. was treated with N,N-diisopropylethylamine (76.3 mg, 103 μL, 0.584 mmol). The reaction was stirred at 25° C. overnight. The reaction was diluted with methylene chloride (20 mL) and was washed with a saturated aqueous ammonium chloride solution (1×50 mL) and a saturated aqueous sodium bicarbonate solution (1×50 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (2% methanol/methylene chloride ramped to 6% methanol/methylene chloride) provided N-(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-N-(2-hydroxy-2-methyl-propyl)-terephthalamide (14.3 mg, 49%) 1H NMR (300 MHz, DMSO-d6) δ ppm 8.85 (t, J=5.27 Hz, 1H) 8.33 (t, J=6.12 Hz, 1H) 8.28 (d, J=8.67 Hz, 1H) 7.91 (s, 4H) 7.99 (s, 1H) 7.54-7.74 (m, 5H) 7.46 (dd, J=8.67, 1.88 Hz, 1H) 6.91 (d, J=1.70 Hz, 1H) 4.54 (s, 1H) 4.40 (d, J=5.46 Hz, 2H) 3.25 (d, J=6.03 Hz, 2H) 1.08-1.14 (m, 6H).

Provenance & Evidence