Heptane → (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 di-D-tartrate

HRID 2369349Notes

Reaction equation

HRID 2369349 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:29]=[C:14]3[C@H:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1.[C:36]([C@H:39]([C@@H:41]([C:43]([O-:45])=[O:44])[OH:42])[OH:40])([O-:38])=[O:37].CCCCCCC>C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.C(O)C>[C:36]([C@H:39]([C@@H:41]([C:43]([OH:45])=[O:44])[OH:42])[OH:40])([OH:38])=[O:37].[C:36]([C@H:39]([C@@H:41]([C:43]([OH:45])=[O:44])[OH:42])[OH:40])([OH:38])=[O:37].[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:29]=[C:14]3[C@H:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:30]1[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 5460284D-TartrateHCID 46854987E-2212

Product 1

HCID 86659212(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 di-D-tartrate

Reagents, catalysts & solvents 1

HCID 86653873D-tartaric acid ethanolSolvent

Procedure

(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 (810.18 mg) was dissolved in 8 mL of a D-tartaric acid-ethanol solution (751.13 mg/10 mL) with stirring at room temperature. The oil was precipitated when 2 mL of heptane was added. Accordingly, the oily substance was dissolved by ultrasonic treatment to prepare a clear solution. Several mg of crystals of the 1.5 D-tartrate prepared according to Example 1 were added, followed by stirring at room temperature. Stirring for about one hour resulted in gelation and subsequent precipitation of a solid. Further, stirring was continued while gradually adding 14 mL of heptane. A part of the suspension (2 mL) was separated and the solid was collected by filtration through a glass filter. The solid was dried under reduced pressure at room temperature to obtain 71.14 mg of the title compound as white solid crystals.

Workup

  1. customThe oil was precipitated when 2 mL of heptane
  2. additionwas added
  3. dissolutionAccordingly, the oily substance was dissolved by ultrasonic treatment
  4. customto prepare a clear solution
  5. additionwere added
  6. stirringby stirring at room temperature
  7. stirringStirring for about one hour
  8. customresulted in gelation and subsequent precipitation of a solid
  9. stirringFurther, stirring
  10. customA part of the suspension (2 mL) was separated
  11. filtrationthe solid was collected by filtration through a glass
  12. filtrationfilter
  13. customThe solid was dried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-3d4cbf876ec44f7e8670bf079014ff90
Source dataset
uspto-grants-2014_04
Patent number
US08703954B2

Reaction notes

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