Methanol → HCID 86653015, compound

HRID 389125Notes

Reaction equation

HRID 389125 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[C:12]1[N:16]([CH3:17])[C:15]([C:18]([CH3:30])([O:20][C:21]2[C:26]([F:27])=[CH:25][C:24]([F:28])=[CH:23][C:22]=2[F:29])[CH3:19])=[N:14][N:13]=1)[C:7]#[N:8].CO.[OH-].[Na+]>[Co](Cl)Cl.C(OCC)(=O)C.O>[ClH:3].[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:7][NH2:8])[CH:9]=[CH:10][C:11]=1[C:12]1[N:16]([CH3:17])[C:15]([C:18]([CH3:19])([O:20][C:21]2[C:22]([F:29])=[CH:23][C:24]([F:28])=[CH:25][C:26]=2[F:27])[CH3:30])=[N:14][N:13]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 58243475HCID 58243475, compound

Product 1

HCID 86653015HCID 86653015, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 24288Cobalt(II) chlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (245 mg) was added to a mixture of 3-chloro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}benzonitrile (438 mg), cobalt chloride (II) hexahydrate (515 mg) and methanol (10 ml), followed by stirring at room temperature for one hour. Water, a 1M aqueous sodium hydroxide solution and ethyl acetate were added to the reaction solution, followed by celite filtration. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 10:1). The resulting residue was dissolved in ethyl acetate, 4M hydrogen chloride-ethyl acetate (2 ml) was added thereto and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate to obtain 1-(3-chloro-4-{4-methyl-5-[1-methyl-1-(2,4,6-trifluorophenoxy)ethyl]-4H-1,2,4-triazol-3-yl}phenyl}methanamine dihydrochloride (141 mg) as a white solid.

Workup

  1. filtrationfollowed by celite filtration
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:1 to 10:1)
  7. dissolutionThe resulting residue was dissolved in ethyl acetate
  8. addition4M hydrogen chloride-ethyl acetate (2 ml) was added
  9. customthe solvent was evaporated under reduced pressure
  10. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-f8ae5a284cbe4941a53f7553c8719182
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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