Sodium Carbonate → HCID 86696526, compound

Participants

Reaction Steps

A solution of thionyl chloride (0.713 mL, 8.23 mmol) and 2-cyclopropylacetic acid (0.247 g, 2.468 mmol) in methylene chloride (10 mL) was heated to reflux for 30 min. The solution was cooled and concentrated. The residue was dissolved in EtOAc (10 mL) and added to a stirred mixture of N-(((1S,2S)-2-(4-fluorophenyl)cyclopropyl)methyl)-2-hydrazinyl-3-(trifluoromethyl)pyridin-4-amine (0.56 g, 1.646 mmol) in EtOAc (10 mL), THF (10 mL), and sat'd Na2CO3 (10 mL). The mixture was stirred for 1 h. The reaction was diluted with EtOAc. The organic layer was separated, washed with aqueous sodium bicarbonate, washed with brine, dried over MgSO4, and concentrated to give the crude product. The crude product was purified by silica gel chromatography to give 2-cyclopropyl-N′-(4-((((1S,2S)-2-(4-fluorophenyl)-cyclopropyl)methyl)amino)-3-(trifluoromethyl)pyridin-2-yl)acetohydrazide (360 mg, 49%) as a light yellow gum. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.90 (d, J=6.0 Hz, 1H), 7.74 (br. s., 1H), 7.09-6.86 (m, 4H), 6.19 (d, J=6.0 Hz, 1H), 5.40-5.16 (m, 1H), 3.34-3.09 (m, 2H), 2.29 (d, J=7.0 Hz, 3H), 1.88 (dt, J=9.1, 4.9 Hz, 2H), 1.44-1.30 (m, 1H), 1.13-1.02 (m, 2H), 1.01-0.93 (m, 1H), 0.72-0.55 (m, 2H), 0.27 (d, J=5.8 Hz, 2H). LCMS M+1=423.2.

Provenance & Evidence