Citric Acid → HCID 69655660, 화합물

HRID 11565

반응식

HRID 11565 반응식
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1)#[N:2].CN1CCOCC1.ClC(OCC(C)C)=O.[C:27]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH2:41])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:30]([O:29][C:27](=[O:28])[NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:7]([C:6]1[CH:5]=[N:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=1)=[O:9])([CH3:33])([CH3:31])[CH3:32]

참가 물질

7

반응물 5

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 27611086-Cyanopyridine-3-carboxylic acid

생성물 1

HCID 69655660HCID 69655660, 화합물수율 78.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
5 °C

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.

후처리

  1. temperatureThe reaction mixture was warmed to rt overnight
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phases were washed with bicarbonate and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-0fe46712cd1942958efdafa5a636c66d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098247B2

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