Thionyl Chloride → HCID 89622571, compound

Participants

Reaction Steps

A solution of Example 68 (60 mg, 164 μmol) in dichloromethane (5 ml) was treated with thionyl chloride (18 μl, 246 μmol). The mixture was stirred at rt for 15 min and then evaporated. The residue was dissolved in ethanol (2 ml) and treated with DIPEA (57 μl, 328 μmol). The mixture was stirred at 60° C. overnight and then heated to 150° C. for 30 min in a microwave device. After this, the mixture was evaporated, and the residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. TFA). The product thus obtained was dissolved in ethanol (2 ml) and again heated to 150° C. for 30 min in the microwave oven. DIPEA (57 μl, 328 μmol) was added, and heating to 150° C. in the microwave oven was continued for further 30 min. After evaporation, the residue was purified by column chromatography on silica gel (dichloromethane/methanol 95:5) affording 16 mg (23% of th.) of the title compound.

Provenance & Evidence