Hydrochloric Acid → HCID 86628810, compound

HRID 2244635Notes

Reaction equation

HRID 2244635 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][N:24]4[CH:27]=[C:28]([CH2:30][C:31]([O:33]CC)=[O:32])[N:29]=[C:23]4[CH:22]=3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([F:14])([F:13])[F:12].[OH-].[Na+].[ClH:40].Cl.CCOC(C)=O>C1COCC1.CCOC(C)=O>[ClH:40].[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][N:24]4[CH:27]=[C:28]([CH2:30][C:31]([OH:33])=[O:32])[N:29]=[C:23]4[CH:22]=3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:15])[C:11]([F:12])([F:13])[F:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 59214348Ethyl (7-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridin-2-yl)acetate

Product 1

HCID 86628810HCID 86628810, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl (7-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridin-2-yl)acetate (230 mg) in THF (2.0 ml) was added a 1M aqueous NaOH solution (1.0 ml), followed by stirring at 80° C. for 2 hours. After cooling to room temperature, a 1 M HCl aqueous solution (1.0 ml) was added thereto, followed by extraction with chloroform. The organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform:CH3OH=10:1 to 5:1) to obtain colorless powders. To a solution of this colorless powder in EtOAc was added a 4M HCl/EtOAc solution, followed by concentration. The resulting colorless powder was powdered/washed with IPE to obtain (7-{5-[3-(trifluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)phenyl]-1,2,4-oxadiazol-3-yl}imidazo[1,2-a]pyridin-2-yl)acetic acid hydrochloride (180.4 mg) as colorless powders.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=10:1 to 5:1)
  7. customto obtain colorless powders
  8. concentrationfollowed by concentration
  9. washThe resulting colorless powder was powdered/washed with IPE

Sources & evidence

ORD record
ord-2436ea7e21364c2c8b93482733e3e972
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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