Hydrogen Bromide → (8S)-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]pyridine dihydrobromide

HRID 2369351Notes

Reaction equation

HRID 2369351 reaction equation
[BrH:1].[CH3:2][O:3][C:4]1[N:9]=[C:8](/[CH:10]=[CH:11]/[C:12]2[N:30]=[C:15]3[C@H:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])[CH2:17][CH2:18][CH2:19][N:14]3[N:13]=2)[CH:7]=[CH:6][C:5]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1.CCCCCCC>C(O)C>[BrH:1].[BrH:1].[CH3:2][O:3][C:4]1[N:9]=[C:8](/[CH:10]=[CH:11]/[C:12]2[N:30]=[C:15]3[C@H:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])[CH2:17][CH2:18][CH2:19][N:14]3[N:13]=2)[CH:7]=[CH:6][C:5]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8900Heptane2×HCID 46854987E-2212

Product 1

HCID 66991574(8S)-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]pyridine dihydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated hydrobromic acid (24.8 μL) was added to a solution of (8S)-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]pyridine (51.42 mg) in ethanol (1 mL), and 1 mL of heptane was added with stirring at room temperature. After several minutes, 1 mL of heptane was further added to the solution and stirring was continued. The solution was stirred at room temperature for one hour and then further stirred at about 5° C. for 20 minutes. The precipitated solid was collected by filtration through a glass filter and dried under reduced pressure at room temperature to obtain 49.24 mg of the title compound as white solid crystals.

Workup

  1. additionwas added
  2. waitAfter several minutes
  3. stirringstirring
  4. stirringThe solution was stirred at room temperature for one hour
  5. stirringfurther stirred at about 5° C. for 20 minutes
  6. filtrationThe precipitated solid was collected by filtration through a glass
  7. filtrationfilter
  8. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-4ff0de4d925a419daa5a0c4a91cb4f8b
Source dataset
uspto-grants-2014_04
Patent number
US08703954B2

Reaction notes

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