Triethylamine → N-(4-(1-acetyl-3-methylpyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide

HRID 13394Notes

Reaction equation

HRID 13394 reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].CS(Cl)(=O)=O.O[CH:14]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[O:28])=[CH:22][C:21]=1[F:35])[CH:15]([CH3:19])[CH2:16][CH2:17]O.C(=O)(O)[O-:37].[Na+]>O.C(Cl)(Cl)Cl>[C:1]([N:3]1[CH2:17][CH2:16][CH:15]([CH3:19])[CH:14]1[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[O:28])=[CH:22][C:21]=1[F:35])(=[O:37])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate3×HCID 23145534N-(4-(1,4-dihydroxy-2-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide

Product 1

HCID 23145589N-(4-(1-acetyl-3-methylpyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

0.18 ml of triethylamine and 0.07 ml of methanesulfonyl chloride were added in order to a chloroform (5 ml) solution of 100 mg of N-(4-(1,4-dihydroxy-2-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 23 mg of sodium azide was added to a dimethylformamide (4 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled to room temperature, water was added to it, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate were added in order to a methanol (5 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 15 minutes. The reaction liquid was cooled to room temperature, and then aqueous saturated sodium bicarbonate was added to it, extracted with chloroform and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 0.08 ml of triethylamine, 0.07 ml of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine were added in order to a chloroform (4 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1) to obtain the entitled compound as a colorless oily substance.

Workup

  1. customthe reaction liquid
  2. extractionextracted with chloroform
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was evaporated away under reduced pressure, and 23 mg of sodium azide
  5. additionwas added to a dimethylformamide (4 ml) solution of the resulting residue
  6. customthe reaction liquid
  7. stirringwas stirred at 40° C. for 2 hours
  8. customThe reaction liquid
  9. temperaturewas cooled to room temperature
  10. extractionextracted with ethyl acetate
  11. dry with materialdried with anhydrous sodium sulfate
  12. customThe solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate
  13. additionwere added in order to a methanol (5 ml) solution of the resulting residue
  14. customthe reaction liquid
  15. stirringwas stirred at 40° C. for 15 minutes
  16. customThe reaction liquid
  17. temperaturewas cooled to room temperature
  18. extractionextracted with chloroform
  19. dry with materialdried with anhydrous sodium sulfate
  20. customThe solvent was evaporated away under reduced pressure, and 0.08 ml of triethylamine, 0.07 ml of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine
  21. additionwere added in order to a chloroform (4 ml) solution of the resulting residue
  22. customthe reaction liquid
  23. stirringwas stirred at room temperature for 30 minutes
  24. extractionextracted with chloroform
  25. dry with materialdried with anhydrous sodium sulfate
  26. customThe solvent was evaporated away under reduced pressure
  27. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
  28. customto obtain the entitled compound as a colorless oily substance

Sources & evidence

ORD record
ord-991453ea36b94f068b0ee0def6cceb06
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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