4-Methylmorpholine → HCID 68157811, compound

Participants

Reaction Steps

To a solution of 3,4-difluoro-N2-phenylbenzene-1,2-diamine (400 mg, 1.8 mmol), Boc-ser(OMe)-OH (800 mg, 2.0 mmol), HOAT (340 mg, 2.0 mmol) and N-methylmorpholine (500 μL, 4.0 mmol) in DCM (5 mL) was added N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (480 mg, 2.0 mmol) and the reaction mixture stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with DCM (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was dissolved in HCl in dioxane (10 mL, 4 M) and the reaction mixture heated at 80° C. for 4 h. The reaction mixture was concentrated in vacuo and the resultant residue dissolved in EtOAc (10 mL). The solution was washed with sat. aq. NaHCO3 and the product extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine, dried (MgSO4), concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, eluting with 0-10% methanol in DCM) to give the title compound as an off white solid (207 mg, 38%). LCMS (Method C): RT=2.27 min, [M+H]+=304.

Provenance & Evidence