1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

HRID 884939

반응식

HRID 884939 반응식
CCN=C=NCCCN(C)C.[C:12]([O:16][C:17]([NH:19][C:20]1[CH:28]=[N:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH2:29][C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=1[OH:40]>N1C=CC=CC=1>[C:12]([O:16][C:17]([NH:19][C:20]1[CH:28]=[N:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:29][C:30]1[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[CH:32][C:31]=1[OH:40])=[O:24])=[O:18])([CH3:13])([CH3:14])[CH3:15]

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1202462-Amino-4-(trifluoromethyl)phenolHCID 212015233-(((Tert-butoxy)carbonyl)amino)pyridine-4-carboxylic acid

생성물 1

HCID 668802523-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide수율 75.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of 1.15 g of WSC and 8 ml of pyridine, 1.43 g of 3-tert-butoxycarbonylamino isonicotinic acid was added and stirred at room temperature for 15 minutes. To the reaction mixture, 1.06 g of 2-amino-4-(trifluoromethyl)phenol was added and stirred while heating at 60° C. for two hours. Thereafter, the mixture reaction was cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 1.79 g of 3-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide.

후처리

  1. additionwas added
  2. stirringstirred
  3. temperaturewhile heating at 60° C. for two hours
  4. customThereafter, the mixture reaction
  5. temperaturewas cooled to room temperature
  6. concentrationconcentrated under reduced pressure
  7. additionWater was added to the residue
  8. extractionfollowed by extraction with ethyl acetate twice
  9. washThe combined organic layers were washed with a saturated sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5427e9634e0a41ef8ae381d1b4fac1bf
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242133B2

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