Dimethylcarbamoyl Chloride → 2-(2,4-difluorophenyl)-3-(2-cyanopyridin-5-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 1196947Notes

Reaction equation

HRID 1196947 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH:16]([C:18]1[CH:19]=[N+:20]([O-])[CH:21]=[CH:22][CH:23]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH3:26][N:27](C)C(Cl)=O.C[Si](C#N)(C)C>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:26]#[N:27])=[N:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 18956537HCID 18956537, compound

Product 1

HCID 189565322-(2,4-difluorophenyl)-3-(2-cyanopyridin-5-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-olYield 18.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of part (i) (0.93 g) and N,N-dimethylcarbamoyl chloride (0.40 g) in dichloromethane (10 ml) was stirred at room temperature overnight. Trimethylsilyl cyanide (0.40 g) was added and stirring was continued for a further 60 hours. The solution was washed with 10% sodium carbonate solution and the aqueous layer was separated and washed with dichloromethane. The organic layers were combined, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel using hexane/isopropanol (4:1) as eluant to give 2-(2,4-difluorophenyl)-3-(2-cyanopyridin-5-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (0.18 g), m.p. 136°-141°.

Workup

  1. stirringstirring
  2. waitwas continued for a further 60 hours
  3. washThe solution was washed with 10% sodium carbonate solution
  4. customthe aqueous layer was separated
  5. washwashed with dichloromethane
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-5ac4373bedf84060a0e0c10169e1da55
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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