Sodium Carbonate → HCID 86696531, compound

Participants

Reaction Steps

To a mixture of trans-N-((2-(4-fluorophenyl)cyclopropyl)methyl)-2-hydrazinyl-N-methyl-3-(trifluoromethyl)pyridin-4-amine (0.5 g, 1.411 mmol) in EtOAc (6 mL), THF (6 mL) and 2.0 M of aqueous sodium carbonate (3.53 mL, 7.06 mmol) was added 3,3,3-trifluoropropionyl chloride (0.248 g, 1.693 mmol) dropwise at rt. The resulting mixture was stirred at under nitrogen for 10 min. The reaction mixture was partitioned between EtOAc/aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed with aqueous sodium bicarbonate (2×20 mL) and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography using 0-30% EtOAc/hexane as the eluent to give trans-3,3,3-trifluoro-N′-(4-(((2-(4-fluorophenyl)cyclopropyl)methyl)(methyl)amino)-3-(trifluoromethyl)pyridin-2-yl)propanehydrazide (0.46 g, 66.7% yield) as a white solid. 1H NMR (500 MHz, METHANOL-d4) δ 7.88 (d, J=6.0 Hz, 1H), 7.08-7.01 (m, 2H), 6.99-6.91 (m, 2H), 6.58 (d, J=6.1 Hz, 1H), 3.41 (dd, J=14.0, 5.6 Hz, 1H), 3.36-3.24 (m, 2H), 3.13 (dd, J=14.0, 7.6 Hz, 1H), 1.81-1.71 (m, 1H), 1.32-1.21 (m, 1H), 0.99 (dt, J=8.6, 5.2 Hz, 1H), 0.87 (dt, J=8.8, 5.4 Hz, 1H). LCMS: M+1=465.13.

Provenance & Evidence