HCID 18956529, compound → 2-(2,4-Difluorophenyl)-3-(pyridin-2-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 2380036Notes

Reaction equation

HRID 2380036 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH3:13])[CH2:11][O:10]1.[Na].[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:10])([CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:13])[CH2:11][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1

Participants

4

Reactant 2

HCID 18956529HCID 18956529, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 193659342-(2,4-Difluorophenyl)-3-(pyridin-2-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of part (i) (2.20 g) and 1H-1,2,4-triazole sodium salt (1.53 g) in N,N-dimethylformamide (15 ml) was heated at 60° with stirring for 18 hours and then evaporated. Water (50 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined extracts were dried (Na2SO4), evaporated and the residue was chromatographed on silica gel. Elution with ethyl acetate first gave, after combination and evaporation of appropriate fractions, the title compound, diastereoisomeric pair A, (0.93 g), m.p. 146°-148° (from ether).

Workup

  1. temperaturewas heated at 60°
  2. customevaporated
  3. additionWater (50 ml) was added
  4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated
  7. customthe residue was chromatographed on silica gel
  8. washElution with ethyl acetate
  9. customfirst gave
  10. customafter combination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-57e96e6fc1814a7f8aec7a9917f0379f
Source dataset
uspto-grants-1994_11
Patent number
US05364938

Reaction notes

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