1,2-Dichloroethane → HCID 68951430, compound

Participants

Reaction Steps

To a solution of (7S)-3-hydroxy-5-methyl-4-oxo-7-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylic acid (246 mg, 0.856 mmol) in DMF (3 mL) were added HOAT (175 mg, 1.28 mmol), and EDC (246 mg, 1.28 mmol). The reaction mixture was stirred at ambient temperature 15 minutes then methyl 2-(aminomethyl)-5-fluorobenzoate hydrochloride (226 mg, 1.03 mmol) and triethylamine (0.13 g, 1.28 mmol) were added. The reaction was stirred at ambient temperature overnight. The solvent was removed in vacuo, and the resulting residue was purified by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the product as a light pink solid. 1H NMR (400 MHz, d6-DMSO) δ 9.60 (bs, 1H), 8.60 (t, J=6.2 Hz, 1H), 7.61 (dd, J=9.5, 2.3 Hz, 1H), 7.45 (m, 2H), 7.36 (m, 3H), 7.04 (d, J=7.1 Hz, 2H), 5.75 (t, J=4.0 Hz, 1H), 4.68 (ABX, J=15.8, 6.2 Hz, 2H), 4.18 (dd, J=13.4, 4.5 Hz, 1H), 3.86 (s, 3H), 3.81 (dd, J=13.4, 4.0 Hz, 1H), 2.88 (s, 3H); ES MS (M+1)-453.

Provenance & Evidence