1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide

HRID 1913707Notes

Reaction equation

HRID 1913707 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:21]=[N:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=O.[NH2:22][C:23]1[CH:28]=[C:27]([C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:24]=1[OH:36]>N1C=CC=CC=1>[Cl:12][C:13]1[CH:21]=[N:20][CH:19]=[CH:18][C:14]=1[C:15]([NH:22][C:23]1[CH:28]=[C:27]([C:29]([F:34])([F:35])[C:30]([F:31])([F:32])[F:33])[CH:26]=[CH:25][C:24]=1[OH:36])=[O:17]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27358163-Chloropyridine-4-carboxylic acidHCID 866510632-Amino-4-(pentafluoroethyl)phenol

Product 1

HCID 866510493-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.44 g of WSC and 4 ml of pyridine, 0.36 g of 3-chloroisonicotinic acid was added. The reaction mixture was stirred at room temperature for 15 minutes. To the reaction mixture, 0.45 g of 2-amino-4-(pentafluoroethyl)phenol was added and stirred while heating at 60° C. for two hours. The reaction mixture 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 water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.25 g of 3-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide.

Workup

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

Sources & evidence

ORD record
ord-85288721b9e9472d910ddf0ddf6f4fba
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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