Water → 2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6-dihydro[1,2,4]triazolo[1,5-a]pyridine

HRID 546794Notes

Reaction equation

HRID 546794 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:30]=[C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])(O)[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1.C(N(S(F)(F)F)CC)C.C(OCC)(=O)C.O>ClCCl>[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:30]=[C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[CH:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluoride2×HCID 576091932-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-ol

Product 1

HCID 576091762-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6-dihydro[1,2,4]triazolo[1,5-a]pyridineYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-{(E)-2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-ol (56 mg) was dissolved in dichloromethane (2 ml). Diethylaminosulfur trifluoride (45 ul) was added under ice-cooling, and the reaction solution was stirred at room temperature for three hours. Thereafter, diethylaminosulfur trifluoride (45 ul) was added again at room temperature, and the reaction solution was further stirred at room temperature overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was separated by CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm; mobile phase: hexane:ethanol=1:1) to obtain the title compound (20 mg). The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. stirringthe reaction solution was further stirred at room temperature overnight
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was separated by CHIRALPAK™ IB

Sources & evidence

ORD record
ord-e394f6103567411b8ce56411ce54604b
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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