Pyridine → HCID 12052640, compound

Participants

Reaction Steps

To a suspension of 4-[2-(2-oxopyrrolidin-1-yl)ethoxy]-benzoic acid (250 mg, 1.0 mmol) in dry dichloromethane (10 mL) was added oxalyl chloride (0.184 mL, 2.1 mmol, 2.1 eq.) then a catalytic amount of DMF. After 1 h, the solvent was removed under reduced pressure. The residue was suspended in dry dichloromethane (9 mL) then added portionwise to a ) solution of N1-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]-1,2-benzenediamine (prepared according to Example 6, Part E) (292 mg, 0.94 mmol, 0.94 eq.) in dry dichloromethane (1 mL) and pyridine (0.182 mL, 2.25 mmol, 2.25 eq.) at 0° C. until all of the aniline had been consumed by tlc (9:1 CHCl3:MeOH). The reaction mixture was allowed to warm to ambient temperature then quenched with the addition of a saturated aqueous solution of sodium bicarbonate (10 mL). The reaction mixture was diluted with ethyl acetate (50 mL) then the layers were separated. The organic layer was dried (MgSO4), filtered, then concentrated under reduced pressure. The amide was obtained as a tan foam (140 mg, 26%) after flash chromatography (2-10% MeOH, 0.5% TEA in CHCl3).

Provenance & Evidence