Hydrochloric Acid → HCID 118378980, compound

HRID 931047Notes

Reaction equation

HRID 931047 reaction equation
[N:1]1([C:6]2[C:7]3[N:8]([C:16]([C:19]([O:21]CC)=[O:20])=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1.C1COCC1.[OH-].[Na+].Cl>O.C(O)C>[N:1]1([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=[O:20])=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118379016ethyl 8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 118378980HCID 118378980, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate (320 mg), THF (4 mL) and ethanol (4 mL) was added 2N aqueous sodium hydroxide solution (0.98 mL), and the mixture was stirred at room temperature 3 hr. The reaction mixture was acidified with 1N hydrochloric acid, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from THF/hexane to give the title compound (270 mg).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from THF/hexane

Sources & evidence

ORD record
ord-85c0992555c642f4a86601f2768d485d
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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