Pyrazine-2-Carboxylic Acid Hydrazide → 7-[(2,3-Dichlorophenyl)carbonyl]-3-(2-pyrazinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889075Notes

Reaction equation

HRID 1889075 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][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].[N:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[C:26]([NH:28][NH2:29])=O>C(O)CCC>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:12][CH2:13][N:14]2[C:26]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][N:20]=3)=[N:28][N:29]=[C:15]2[CH2:16]1)=[O:10]

Participants

4

Reactant 2

HCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 665989011-[(2,3-Dichlorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazine

Product 1

HCID 665991987-[(2,3-Dichlorophenyl)carbonyl]-3-(2-pyrazinyl)-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-[(2,3-dichlorophenyl)carbonyl]-5-(ethyloxy)-1,2,3,6-tetrahydropyrazine (0.48 g, 1.594 mmol, e.g. prepared as described below) and 2-pyrazinecarbohydrazide (0.242 g, 1.753 mmol, CAS [768-05-8], commercially available e.g. from TimTec, J & W PharmLab or AKos Consulting) in anhydrous n-butanol (3.19 ml) was heated to reflux under argon atmosphere. After 2 hours the reaction was cooled to room temperature and concentrated in vacuo. The residue was purified by mass-directed automated (preparative) HPLC (MDAP) to give pure 7-[(2,3-dichlorophenyl)carbonyl]-3-(2-pyrazinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.260 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon atmosphere
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified

Sources & evidence

ORD record
ord-c9a8bc46f3c744cf9b3f0a5a585bae01
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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