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To a solution of pyridine-4-carboxylic acid (1.0 g) and triethylamine (1.2 ml) in toluene (20 ml) was added diphenylphosphoryl azide (1.75 ml) at ambient temperature. The resulting mixture was heated to reflux for 30 minutes and cooled to 0° C. To the mixture was added 1-tert-butoxycarbonylpiperazine (1.51 g), and the mixture was allowed to heat to 90° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was taken up into ethyl acetate, washed in turn with water and brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was chromatographed on silica gel (150 ml) eluting with 0-7% methanol in dichloromethane. Trituration with a mixture of diisopropyl ether and ethanol gave 1-tert-butoxycarbonyl-4-(pyridin-4-ylcarbamoyl)piperazine (0.66 g).

1. temperatureThe resulting mixture was heated
2. temperatureto reflux for 30 minutes
3. temperatureto heat to 90° C. for 1 hour
4. temperatureAfter cooling to ambient temperature
5. washwashed in turn with water and brine
6. dry with materialdried over magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was chromatographed on silica gel (150 ml)
9. washeluting with 0-7% methanol in dichloromethane
10. additionTrituration with a mixture of diisopropyl ether and ethanol