1-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)- → (2R,3R)-3-(5-chloro-3',6'-dihydro-2,4'-bipyridin-1'(2'H)-yl)-2(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol

HRID 1009067Notes

Reaction equation

HRID 1009067 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=2)=[N:24][CH:25]=1.O.O.O.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH2:27][CH2:28][N:29]([C@H:11]([CH3:12])[C@:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])([OH:10])[CH2:13][N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)[CH2:30][CH:31]=2)=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 211055245-Chloro-1',2',3',6'-tetrahydro-2,4'-bipyridineHCID 23708903Lithium perchlorate trihydrate

Product 1

HCID 44538606(2R,3R)-3-(5-chloro-3',6'-dihydro-2,4'-bipyridin-1'(2'H)-yl)-2(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-olYield 63.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (0.76 g, 3.0 mmol) and 5-chloro-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (1.31 g, 6.7 mmol) were dissolved in acetonitrile (20 ml), and lithium perchlorate trihydrate (1.50 g, 9.3 mmol) was added thereto and refluxed for 40 hours. The solvent was evaporated under a reduced pressure, and the thus obtained residue was dissolved in ethyl acetate and washed with water. The solvent was again evaporated under a reduced pressure, and the residue was purified using a silica gel column to obtain 0.88 g of the intended substance (yield 63.8%).

Workup

  1. temperaturerefluxed for 40 hours
  2. customThe solvent was evaporated under a reduced pressure
  3. dissolutionthe thus obtained residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe solvent was again evaporated under a reduced pressure
  6. customthe residue was purified
  7. customto obtain 0.88 g of the intended substance (yield 63.8%)

Sources & evidence

ORD record
ord-3e3e30816abe4e6d94f4ba69de98aea9
Source dataset
uspto-grants-2011_07
Patent number
US07973056B2

Reaction notes

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