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

HRID 2104133Notes

Reaction equation

HRID 2104133 reaction equation
O[C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][C:15]([NH:18][NH:19][C:20]([C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)=O)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.P(Cl)(Cl)([Cl:30])=O>CC#N>[Cl:30][C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][C:15]3=[N:18][N:19]=[C:20]([C:22]4[CH:27]=[N:26][CH:25]=[CH:24][N:23]=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 178523946HCID 178523946, compound

Product 1

HCID 578054793-Chloro-2-phenyl-9-pyrazin-2-yl[1,2,4]triazolo[4',3':1,6]pyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
100 °C

Procedure

To a microwave vial was added N′-(2-hydroxy-3-phenylpyrido[2,3-b]pyrazin-6-yl)pyrazine-2-carbohydrazide (8-4, 0.412 g, 1.147 mmol), MeCN (5.0 mL), and finally phosphorus oxychloride (0.687 mL, 7.37 mmol). The reaction mixture was then heated to 100° C. in a hot oil bath (capped) overnight. The reaction mixture was then permitted to cool to room temperature, diluted with MeCN & concentrated in vacuo. The resulting residue was then suspended in ethyl acetate, washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 8-5 as a brown solid. HRMS (M+H)+: observed=360.0773, calculated=360.0759.

Workup

  1. custom(capped) overnight
  2. temperatureto cool to room temperature
  3. concentrationconcentrated in vacuo
  4. washwashed with a saturated solution of sodium bicarbonate
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb5209b462474b4d959dc4206b4051f4
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

Loading…