1-Hydroxybenzotriazole → HCID 54765736, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-3-Cyclopentyl-2-(3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionic acid (200 mg, 0.61 mmol) in methylene chloride (10 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI-HCl) (130 mg, 0.67 mmol), 1-hydroxybenzotriazole (HOBT) (90 mg, 0.67 mmol) and commercially available 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (114 mg, 0.73 mmol). The reaction mixture was stirred for 18 hours at 25° C., under N2. The reaction mixture was diluted with methylene chloride, washed with 2N HCl, saturated sodium bicarbonate solution, and a saturated sodium chloride solution and dried over magnesium sulfate. The crude product obtained after concentration was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 12 g; (0% to 100% ethyl acetate/hexane) to afford (S)-3-Cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionamide as a white powder, 205 mg (72% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04 (br. s., 3 H), 1.06 (br. s., 3 H), 1.09-1.83 (m, 10 H), 1.83-1.97 (m, 1 H), 3.75 (s, 2 H), 3.89 (s, 2 H), 4.03 (d, J=19.2 Hz, 1 H), 4.40 (d, J=19.2 Hz, 1 H), 4.67 (s, 1 H), 4.87 (dd, J=10.3, 4.8 Hz, 1 H), 6.44 (d, J=1.8 Hz, 1 H), 7.03-7.15 (m, 2 H), 7.20-7.28 (m, 2 H), 7.53 (d, J=1.8 Hz, 1 H), 10.86 (s, 1 H).

Provenance & Evidence