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

HRID 1196919Notes

Reaction equation

HRID 1196919 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-e77016be0268493b95e23999c91a213b
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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