Potassium Carbonate → [5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-acetic acid

HRID 554672Notes

Reaction equation

HRID 554672 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([OH:31])=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH2:22][N:23]([C:26]([CH:28]2[CH2:30][CH2:29]2)=[O:27])[CH2:24][CH3:25])[CH:11]=1)C.S(C1C=CC(C)=CC=1)(O[CH2:37][C:38]([F:41])([F:40])[F:39])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:28]1([C:26]([N:23]([CH2:22][C:13]2[CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=[CH:17][C:12]=2[C:10]2[CH:11]=[C:6]([CH2:5][C:4]([OH:3])=[O:32])[CH:7]=[N:8][C:9]=2[O:31][CH2:37][C:38]([F:41])([F:40])[F:39])[CH2:24][CH3:25])=[O:27])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)2×HCID 178470738HCID 178470738, compound

Product 1

HCID 45139199[5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-hydroxy-pyridin-3-yl)-acetic acid ethyl ester (0.175 g, 0.39 mmol), 2,2,2-trifluoroethyl tosylate (0.151 g, 0.58 mmol), and potassium carbonate (0.070 g, 0.51 mmol) were combined in DMF (1.8 mL) and stirred at 55° C. overnight. Additional 2,2,2-trifluoroethyl tosylate and potassium carbonate were added, and the reaction was stirred at 75° C. overnight. After cooling, the crude material was used directly in the hydrolysis step. The ester was hydrolyzed to the acid as described in Example 3, Step 7. The acid was purified by preparative HPLC.

Workup

  1. stirringthe reaction was stirred at 75° C. overnight
  2. temperatureAfter cooling
  3. customThe acid was purified by preparative HPLC

Sources & evidence

ORD record
ord-2287b67b28e0447188e154ef4bab1ec2
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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