Methylamine → HCID 59540619, compound

Participants

Reaction Conditions

Reaction Steps

1-{3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-3-methyl-pyrrolidine-3-carboxylic acid methylamide was prepared by treating 1-{3-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-3-methyl-pyrrolidine-3-carboxylic acid methyl ester (190 mg, 0.3 mmol) with methanol (3 mL) and potassium hydroxide (2 mL, 0.5 M aqueous). Upon partitioning the mixture between 10% aqueous acetic acid and ethyl acetate, the desired acid (110 mg, 0.27 mmol) was dissolved in N,N-dimethylformamide (3 mL) and treated with carbonyl diimidazole (46 mg, 0.28 mmol) and heated to 65° C. for 2 hours. Methylamine (2 mL) was condensed at −20° C. in heavy-walled vessel. The mixture above was added and the vessel was immediately sealed and heated to 50° C. for 5 days. Upon cooling, the volatiles were removed in vacuo and the residue partitioned between 2% aqueous acetic acid and ethyl acetate. The combined organic layers were aged over anhydrous sodium sulfate. The title compound was obtained as a powder (26 mg) following silica gel chromatography (eluant: 40 to 100% ethyl acetate-hexanes): m.p. 252-254° C.; MS m/z 419 (M+H).

Provenance & Evidence