반응 #11661

반응 방정식

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

수율 78.3%

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction mixture was warmed to rt overnight
2. 2
   추출The aqueous phase was extracted with ethyl acetate
3. 3
   세척the combined organic phases were washed with bicarbonate and brine
4. 4
   건조dried over Na2SO4
5. 5
   기타The solvent was evaporated

실험 절차

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.

출처