Phosphorus oxychloride → HCID 76849760, compound

HRID 245695Notes

Reaction equation

HRID 245695 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86674650HCID 86674650, compound

Product 1

HCID 76849760HCID 76849760, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To N-((3-chloropyrazin-2-yl)methyl)-4-methylpiperazine-1-carboxamide (485 mg) in acetonitrile (3 mL) under a N2 flow was added phosphorus oxychloride (878 μl) and heated at 60° C. (bath temperature) for five hours and at 80° C. for one hour. Then the reaction mixture was concentrated in vacuo. Toluene was added and the mixture was concentrated in vacuo. Residue was taken up with acetonitrile, 7N ammonia in methanol was added with cooling and the suspension was stirred for 16 hours, then filtered and the filtrate concentrated in vacuo. Dichloromethane was added to the residue, again filtered and the filtrate concentrated in vacuo to give 8-chloro-3-(4-methylpiperazin-1-yl)imidazo[1,5-a]pyrazine (400 mg).

Workup

  1. concentrationThen the reaction mixture was concentrated in vacuo
  2. additionToluene was added
  3. concentrationthe mixture was concentrated in vacuo
  4. additionwas added
  5. temperaturewith cooling
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. additionDichloromethane was added to the residue
  9. filtrationagain filtered
  10. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-946d2f9f7f834c2090bb794bd9aba4e2
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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