Sulfuric Acid → (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 disulfate

HRID 2369350Notes

Reaction equation

HRID 2369350 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[CH3:6][O:7][C:8]1[N:13]=[C:12](/[CH:14]=[CH:15]/[C:16]2[N:34]=[C:19]3[C@H:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH2:21][CH2:22][CH2:23][N:18]3[N:17]=2)[CH:11]=[CH:10][C:9]=1[N:35]1[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]1.C(OCC)(=O)C>C(O)C>[S:1]([O:3][S:1]([OH:4])(=[O:3])=[O:2])([OH:2])(=[O:5])=[O:4].[CH3:6][O:7][C:8]1[N:13]=[C:12](/[CH:14]=[CH:15]/[C:16]2[N:34]=[C:19]3[C@H:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH2:21][CH2:22][CH2:23][N:18]3[N:17]=2)[CH:11]=[CH:10][C:9]=1[N:35]1[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 46854987E-2212

Product 1

HCID 66990750(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 disulfate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated sulfuric acid (11.5 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 (98.09 mg) in ethanol (1 mL), and 1 mL of ethyl acetate was added with stirring at room temperature. Since the oily portion was confirmed on the bottom of the recovery flask, the oily substance was dissolved by ultrasonic treatment. Stirring at room temperature under shading for about 30 minutes resulted in precipitation of a solid. The solid was collected by filtration through a glass filter and dried under reduced pressure at room temperature to obtain 127.94 mg of the title compound as white solid crystals.

Workup

  1. additionwas added
  2. dissolutionthe oily substance was dissolved by ultrasonic treatment
  3. stirringStirring at room temperature under shading for about 30 minutes
  4. customresulted in precipitation of a solid
  5. filtrationThe solid was collected by filtration through a glass
  6. filtrationfilter
  7. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-568566e960fb46ab99581cd931321093
Source dataset
uspto-grants-2014_04
Patent number
US08703954B2

Reaction notes

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