Triethyloxonium tetrafluoroborate → 2-(7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridinol

HRID 1889088Notes

Reaction equation

HRID 1889088 reaction equation
F[B-](F)(F)F.C([O+](CC)CC)C.[Cl:13][C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:24]([N:26]1[CH2:31][CH2:30][NH:29][C:28](=O)[CH2:27]1)=[O:25].[OH:33][C:34]1[C:35]([C:40]([NH:42][NH2:43])=O)=[N:36][CH:37]=[CH:38][CH:39]=1>ClCCl>[Cl:13][C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:15]=1[C:24]([N:26]1[CH2:31][CH2:30][N:29]2[C:40]([C:35]3[C:34]([OH:33])=[CH:39][CH:38]=[CH:37][N:36]=3)=[N:42][N:43]=[C:28]2[CH2:27]1)=[O:25]

Participants

5

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 450830583-Hydroxypyridine-2-carbohydrazideHCID 665992084-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-piperazinone

Product 1

HCID 1363723802-(7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazin-3-yl)-3-pyridinol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyloxonium tetrafluoroborate (204 mg, 1.076 mmol) was added to a solution of the 4-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-piperazinone (I1)(300 mg, 0.978 mmol) in Dichloromethane (DCM) (6 mL) and the reaction was stirred for 1 h. To this was added the 3-hydroxy-2-pyridinecarbohydrazide (I93) (180 mg, 1.174 mmol) and the reaction was stirred for 2 hrs. The solvent was evaporated and 1-butanol (6.00 mL) was added. The mixture was heated at reflux for 3 h. After cooling the solvent was evaporated and the residue was partitioned between water/EtOAc. The organic layer was passed through a phase sep. cartridge and the solvent evaporated to afford an amber oil. This was purified by MDAP to afford a colourless solid of desired material in 90 mg.

Workup

  1. stirringthe reaction was stirred for 2 hrs
  2. customThe solvent was evaporated
  3. addition1-butanol (6.00 mL) was added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 3 h
  6. temperatureAfter cooling the solvent
  7. customwas evaporated
  8. customthe residue was partitioned between water/EtOAc
  9. customcartridge and the solvent evaporated
  10. customto afford an amber oil
  11. customThis was purified by MDAP
  12. customto afford a colourless solid of desired material in 90 mg

Sources & evidence

ORD record
ord-1f47c7e5cf9c47aa861a6a7619b4c2ae
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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