Morpholine → HCID 66580649, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-cyano-1-phenyl-1,4-dihydrothiochromeno[4,3-c]pyrazole-3-carboxylate 5,5-dioxide (50 mg, 0.135 mmol) in dry DCM (10 mL) are added morpholine (0.02 mL, 0.156 mmol) and TEA (0.03 mL, 0.196 mmol) after which reaction mixture is cooled to 0° C. EDC.HCl (38 mg, 0.196 mmol) and HOBt (2 mg, 0.013 mmol) are then added to the reaction mixture which is stirred at RT for 12 h under nitrogen. After this time, DCM is added and organic phase is washed with Na2CO3 sat, dried over Na2SO4 concentrated under reduced pressure and purified by silica gel column chromatography (3% MeOH in DCM) to afford the title compound as a pale yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.89 (s, 1H), 7.63-7.60 (m, 3H), 7.55-7.44 (m, 4H), 6.84-6.82 (d, J=7.8 Hz, 1H), 5.74 (s, 2H), 4.78 (s, 2H), 3.97 (m, 2H), 3.66-3.61 (m, 6H). MS (ESI+): 453.0. HPLC (max plot) 96.54%; Rt 3.98 min.

Provenance & Evidence