Dimethylformamide → HCID 89964943, compound

Participants

Reaction Steps

To a solution of CDI (41.3 mg, 0.255 mmol) in DCM (0.25 mL) was added (S)-1,1,1-trifluoropropan-2-amine (0.026 mL, 0.255 mmol). The round bottom flask was then sealed, and the mixture was stirred at room temperature for 2.5 h. A solution of 4-(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-amine (50.0 mg, 0.170 mmol) and DIEA (0.058 mL, 0.340 mmol) in DCM (1 mL) was then added, and the reaction was stirred at room temperature for 20 h. The reaction was diluted with DMF, filtered through a syringe filter, and the reaction purified by RPHPLC (Gemini Axia C18 50×150 mm column, gradient elution 10-100% MeCN/0.1% TFA in H2O). The product containing fractions were combined and the solvent removed by lyophilization to give the title compound as a white solid. MS (ESI, positive ion) m/z: 433.9 (MH+). 1H NMR (300 MHz, d4-MeOH) δ: 8.18-8.29 (m, 1H), 7.64-7.71 (m, J=8.2 Hz, 2H), 7.59 (br. s., 1H), 7.47-7.56 (m, 1H), 7.34-7.47 (m, J=8.3 Hz, 2H), 4.25-4.46 (m, 2H), 4.06 (ddd, J=11.9, 9.6, 2.6 Hz, 1H), 3.02-3.20 (m, 1H), 2.54-2.72 (m, 1H), 1.19-1.30 (m, 3H).

Provenance & Evidence