Benzoylhydrazine → 7-[(2-Chloro-4-fluorophenyl)carbonyl]-3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889072Notes

Reaction equation

HRID 1889072 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][C:15](OCC)=[N:14][CH2:13][CH2:12]1)=[O:10].[C:20]([NH:28][NH2:29])(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:12][CH2:13][N:14]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:28][N:29]=[C:15]2[CH2:16]1)=[O:10]

Participants

4

Reactant 2

HCID 11955Benzoylhydrazine2×HCID 665994581-[(2-Chloro-4-fluorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazine

Product 1

HCID 665989827-[(2-Chloro-4-fluorophenyl)carbonyl]-3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1-[(2-chloro-4-fluorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazine (0.228 g, 0.8 mmol, e.g. see preparation below) and benzohydrazide (benzoylhydrazine, 0.109 g, 0.800 mmol, CAS [613-94-5], commercially available e.g. from Sigma-Aldrich or ABCR) in 1-butanol (1 ml) was heated at reflux for 18 hours. After cooling to room temperature the solvent was evaporated and the residue was purified by mass-directed automated (preparative) HPLC (MDAP). A trituration with diethyl ether was then carried out to yield 7-[(2-chloro-4-fluorophenyl)carbonyl]-3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.053 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customwas evaporated
  4. customthe residue was purified

Sources & evidence

ORD record
ord-fb291f9b2cd948fe8e33988fda315b12
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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