Potassium Carbonate → HCID 68414910, compound

Participants

Reaction Steps

To acid (36) (100 mg, 0.53 mmol) was added thionyl chloride (0.5 mL), a catalytic amount of DMF (1 drop) and the reaction heated at 50° C. for 30 minutes. After cooling the solvent was concentrated in vacuo and azeotroped with toluene to provide the in situ acid chloride. To the acid chloride was added amine (38) (95 mg, 0.53 mmol) and DIPEA (69 mg, 0.53 mmol) in DCM (2 mL), and the reaction mixture stirred at ambient temperature overnight. K2CO3 (aq) was then added and the aqueous layer extracted with DCM. The organic layer was washed with water, dried (Na2SO4) and the solvent concentrated in vacuo. The residue was partially purified using column chromatography eluting with 50% EtOAc in heptane to give the title compound. Yield: 35 mg, 19%; LC-MS tr 1.67 min; HPLC Purity: 52%; MS (ES+) m/z 349 (M+H)

Provenance & Evidence