Dimethylformamide → HCID 68982731, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-[2-(3-aminopropoxy)-4-methylsulfinyl-benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (650 mg, 1.33 mmol), DMF (10 mL) and K2CO3 (552 mg, 4.0 mmol) was added 1,4-dibromobutane (0.16 mL, 1.33 mmol) and the mixture was heated to 80° C. for 5 h. The reaction mixture was cooled, diluted with EtOAc and water, and partitioned. The organic layer was concentrated and chromatographed (250 g of SiO2, CH2Cl2 to 5% of 2 M NH3/MeOH in CH2Cl2) to give impure product. This material was HPLC on a Vydac C18 column [5% CH3CN/(0.1% TFA in H2O) to 70% CH3CN/(0.1% TFA in H2O); Rt: 26.1 m] to give the desired product as a white solid (279 mg, 36%).

Provenance & Evidence