Triethyloxonium tetrafluoroborate → 7-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-3-[4-(methyloxy)-2-pyridinyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889095

Reaction equation

HRID 1889095 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=O)[CH2:13]1)=[O:11].F[B-](F)(F)F.C([O+](CC)CC)C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([C:39]([NH:41][NH2:42])=O)[CH:34]=1>ClCCl>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[C:39]([C:35]3[CH:34]=[C:33]([O:32][CH3:31])[CH:38]=[CH:37][N:36]=3)=[N:41][N:42]=[C:14]2[CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 109539124-Methoxypyridine-2-carbohydrazideHCID 665993614-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone

Product 1

HCID 665994357-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-3-[4-(methyloxy)-2-pyridinyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-[(2,4-dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37) (0.25 g, 0.859 mmol) in anhydrous Dichloromethane (DCM) (2.147 ml) was added triethyloxonium tetrafluoroborate (0.179 g, 0.945 mmol) and the mixture was stirred overnight at room temperature under argon. The white suspension turned to a solution and 4-(methyloxy)-2-pyridinecarbohydrazide (0.158 g, 0.945 mmol, commercially available from e.g. Matrix Scientific, Anichem or 3B Scientific) was added at once. It was a suspension at first but straight after it changed to a yellow solution. After ½ hour a precipitate formed again. LCMS showed that the major product was the intermediate and very little unreacted starting amide was present.

Workup

  1. customAfter ½ hour a precipitate formed again

Sources & evidence

ORD record
ord-5f4f1ee763684027ba4d1777055f5b50
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Linked notes

Loading…