HCID 67975224, compound → HCID 67975438, compound

HRID 623870Notes

Reaction equation

HRID 623870 reaction equation
[CH3:1][C:2]([CH3:38])([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:22](COCC[Si](C)(C)C)[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)=[CH:17][N:16]=2)=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4]>FC(F)(F)C(O)=O.O>[CH3:1][C:2]([CH3:38])([CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:25][C:24]([C:26]([F:28])([F:27])[F:29])=[CH:23][N:22]=3)=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 1

HCID 67975224HCID 67975224, compound

Product 1

HCID 67975438HCID 67975438, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

In trifluoroacetic acid (2.9 mL) and water (0.3 mL) was dissolved methyl 2,2-dimethyl-3-(4-{5-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]pyridin-2-yl}phenoxy)propanoate (144 mg) under ice-cooling, and the mixture was stirred at room temperature overnight. To the residue obtained by concentrating the reaction mixture under reduced pressure were added chloroform and a saturated aqueous sodium bicarbonate solution. The formed insoluble material was dissolved in methanol and combined with the organic layer. The organic layer was washed with water, and concentrated under reduced pressure. The obtained residue was pulverized by cooled ether, collected by filtration and dried to obtain methyl 2,2-dimethyl-3-(4-{5-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyridin-2-yl}phenoxy)-propanoate (85.9 mg).

Workup

  1. temperaturecooling
  2. customTo the residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. additionwere added chloroform
  5. dissolutionThe formed insoluble material was dissolved in methanol
  6. washThe organic layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. temperatureby cooled ether
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-7edcbea578c44e37bb08250e35d05b5d
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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