Triethylamine → HCID 56952649, compound

HRID 1844515Notes

Reaction equation

HRID 1844515 reaction equation
CCOC(C)=O.[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18](CNC(=O)OC(C)(C)C)=[CH:17][CH:16]=2)=[N:12][CH:13]=1.[CH2:30]([N:32](CC)CC)C.[F:37][C:38]1[C:46]([F:47])=[C:45]([F:48])[CH:44]=[CH:43][C:39]=1[C:40](Cl)=[O:41]>O>[F:37][C:38]1[C:46]([F:47])=[C:45]([F:48])[CH:44]=[CH:43][C:39]=1[C:40]([NH:7][C:8]1[CH:13]=[N:12][C:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([NH:32][CH3:30])=[CH:19][CH:20]=2)=[CH:10][CH:9]=1)=[O:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27340222,3,4-Trifluorobenzoyl chlorideHCID 86698880HCID 86698880, compound

Product 1

HCID 56952649HCID 56952649, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an AcOEt (10 mL) solution of tert-butyl {4-[(5-aminopyridin-2-yl)oxy]phenyl}methylcarbamate (0.50 g) and triethylamine (0.32 g) was added 2,3,4-trifluorobenzoyl chloride (0.37 g) at 0° C. The mixture was stirred at room temperature for 1 hour. The mixture was poured into water and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (10 mL), then added TFA (3 mL). After stirring at room temperature for 2 hours, the mixture was poured into saturated aqueous NaHCO3 and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford the title compound (0.55 g) as a white solid.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water, saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  6. stirringAfter stirring at room temperature for 2 hours
  7. additionthe mixture was poured into saturated aqueous NaHCO3
  8. extractionextracted with AcOEt
  9. washThe organic layer was washed with water, saturated aqueous NaCl
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1)

Sources & evidence

ORD record
ord-afe16ebfac154ba3901865f595db8a4a
Source dataset
uspto-grants-2015_02
Patent number
US08946437B2

Reaction notes

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