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

HRID 2094457

Reaktionsgleichung

Reaktionsgleichung von HRID 2094457
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 668802523-tert-butoxycarbonylamino-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamideAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6ef4821b0e154a77ab468bab607e4301
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445522B2

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