Hydrochloric Acid → HCID 67024751, compound

HRID 389154Notes

Reaction equation

HRID 389154 reaction equation
C[Mg]Br.[C:4]1(C)C=CC=CC=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[C:20]1[N:24]([CH3:25])[C:23]([C:26]([CH3:38])([O:28][C:29]2[C:34]([F:35])=[CH:33][C:32]([F:36])=[CH:31][C:30]=2[F:37])[CH3:27])=[N:22][N:21]=1)[CH:15]=[O:16].[Cl-:39].[NH4+].Cl.O1CCOCC1.Cl>C1COCC1.C(OCC)(=O)C>[ClH:39].[F:11][C:12]1[CH:13]=[C:14]([CH:15]([OH:16])[CH3:4])[CH:17]=[CH:18][C:19]=1[C:20]1[N:24]([CH3:25])[C:23]([C:26]([CH3:38])([O:28][C:29]2[C:30]([F:37])=[CH:31][C:32]([F:36])=[CH:33][C:34]=2[F:35])[CH3:27])=[N:22][N:21]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 204431481,4-Dioxane hydrochlorideHCID 58243665HCID 58243665, compoundHCID 178424247HCID 178424247, compound

Product 1

HCID 67024751HCID 67024751, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A 1.4M methylmagnesium bromide/toluene solution (0.5 ml) was added to a solution of 3-fluoro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzaldehyde (90 mg) in THF (1 ml) under ice cooling, followed by stirring for one hour under ice cooling. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was then evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) to obtain 87 mg of a light yellow amorphous. The resulting amorphous was dissolved in ethyl acetate, a 4M hydrogen chloride/1,4-dioxane solution (0.2 ml) was added thereto so as to be hydrochloride. Ethyl acetate was added to the solid obtained by concentration and drying, followed by collecting by filtration, washing with ethyl acetate and drying under reduced pressure to obtain 1-(3-fluoro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}phenyl)ethanol monohydrochloride (83 mg) as a beige solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10)
  6. customto obtain 87 mg of a light yellow amorphous
  7. customobtained by concentration
  8. customdrying
  9. filtrationby collecting by filtration
  10. washwashing with ethyl acetate
  11. customdrying under reduced pressure

Sources & evidence

ORD record
ord-902e45a107514693b9b376fc201310fb
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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