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

HRID 884939

Reaction equation

HRID 884939 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5427e9634e0a41ef8ae381d1b4fac1bf
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Linked notes

Loading…