Reacción #11661

Ecuación de reacción

mono-boc-ortho-phenylenediamine

citric acid

6-cyano-nicotinic acid

N-methylmorpholine

isobutyl chloroformate

→

{2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

Rendimiento 78.3%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was warmed to rt overnight
2. 2
   ExtracciónThe aqueous phase was extracted with ethyl acetate
3. 3
   Lavadothe combined organic phases were washed with bicarbonate and brine
4. 4
   Secadodried over Na2SO4
5. 5
   OtroThe solvent was evaporated

Procedimiento

To a solution of 444 mg (3.0 mmol) 6-cyano-nicotinic acid and 354 mg (3.5 mmol) N-methylmorpholine in 7 ml DMF at −20° C. was added 450 mg (3.3 mmol) isobutyl chloroformate. The reaction mixture was warmed to 5° C., and 625 mg (3.0 mmol) mono-boc-ortho-phenylenediamine was added. The reaction mixture was warmed to rt overnight and then poured into 50 ml 5% aqueous citric acid. The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with bicarbonate and brine and dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (petrol ether/ethyl acetate 2:1) to yield 795 mg (2.35 mmol) {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; mp.183–184° C.

Fuente