Potassium Carbonate → HCID 46945254, compound

HRID 2388311Notes

Reaction equation

HRID 2388311 reaction equation
FC(F)(F)C([NH:5][C:6]1[C:7]([CH:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:21][CH:20]([NH:22][C:23]([CH2:25][NH:26][C:27](=[O:38])[C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=4)=[O:24])[CH2:19]3)[CH2:14][CH2:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:5][C:6]1[C:7]([CH:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:21][CH:20]([NH:22][C:23]([CH2:25][NH:26][C:27](=[O:38])[C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=4)=[O:24])[CH2:19]3)[CH2:16][CH2:17]2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 46945252HCID 46945252, compound

Product 1

HCID 46945254HCID 46945254, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[(1-{4-[3-(2,2,2-Trifluoro-acetylamino)-pyridin-2-yl]-cyclohexyl}-azetidin-3-ylcarbamoyl)-methyl]-3-trifluoromethyl-benzamide (0.042 g, 0.073 mmol, as prepared in Example 17: Step B) was dissolved in methanol (3 mL), treated with a solution of powdered potassium carbonate (1.103, 0.730 mmol) in water (3 mL), and stirred at ambient temperature for 5 d, then heated to 70° C. under reflux condenser for 18 h. After removing the methanol in vacuo, the reaction was diluted with water and extracted thrice with 3:1 EtOAc/2-PrOH. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo giving the title compound as a beige solid.

Workup

  1. temperatureheated to 70° C.
  2. temperatureunder reflux condenser for 18 h
  3. customAfter removing the methanol in vacuo
  4. additionthe reaction was diluted with water
  5. extractionextracted thrice with 3:1 EtOAc/2-PrOH
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5880aa61e6a64d1e9429e355aa5da48c
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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