Phosphorus oxychloride → 3-Chloro-2-phenyl-9-(3-pyridinyl)[1,2,4]triazolo[4',3':1,6]pyrido-[2,3-b]pyrazine

HRID 221988Notes

Reaction equation

HRID 221988 reaction equation
O[C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][C:15]([NH:18][NH:19][C:20](=O)[C:21]3[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=3)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O=P(Cl)(Cl)[Cl:30]>C(#N)C>[Cl:30][C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][C:15]3=[N:18][N:19]=[C:20]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[N:14]3[C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178523945N'-(2-hydroxy-3-phenylpyrido[2,3-b]pyrazin-6-yl)nicotinohydrazide

Product 1

HCID 866526523-Chloro-2-phenyl-9-(3-pyridinyl)[1,2,4]triazolo[4',3':1,6]pyrido-[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of N′-(2-hydroxy-3-phenylpyrido[2,3-b]pyrazin-6-yl)nicotinohydrazide (3-4) (5.8 g, 16.2 mmol) in acetonitrile (1.3 mL) was added POCl3 (7.5 mL, 81 mmol), and stirred at 100° C. for overnight. The solvent was removed under reduced pressure, and to the residue was added CHCl3 and water. The organic layer was separated, dried (Na2SO4), filtered, and evaporated in vacuo. To the residue was added CHCl3, and the resulting solid was collected by filtration to yield 3-chloro-2-phenyl-9-(3-pyridinyl)[1,2,4]triazolo[4′,3′:1,6]pyrido[2,3-b]pyrazine (3-5) as an orange solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionto the residue was added CHCl3 and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. additionTo the residue was added CHCl3
  8. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-a33d3a20a0fc4d15b3082d8170de1785
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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