Phosphorus oxychloride → HCID 58558030, compound

HRID 1969633Notes

Reaction equation

HRID 1969633 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[N:15][C:16]([NH:20][CH2:21][C:22]([NH2:24])=O)=[CH:17][N:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].O=P(Cl)(Cl)Cl>C(Cl)Cl.CO>[S:1]([N:11]1[C:19]2[N:18]=[CH:17][C:16]3[N:15]([C:22]([NH2:24])=[CH:21][N:20]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58557617HCID 58557617, compound

Product 1

HCID 58558030HCID 58558030, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To 2-(5-tosyl-5H-pyrrolo[3,2-b]pyrazin-2-ylamino)acetamide (0.845 g, 2.45 mmol, prepared using E from Preparation #S.1.1 and HCl) under nitrogen was added POCl3 (5.0 mL, 54 mmol). After about 15 min, a reflux condenser was attached and the mixture was warmed to about 100° C. After about 2 h, the solution was allowed to cool to ambient temperature. The mixture was concd under reduced pressure. The residue was slurried in DCM (10 mL) and slowly treated with MeOH (10 mL). The reaction mixture was stirred for about 5 min then concd under reduced pressure. The residue was dissolved in MeOH (20 mL) and then concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (5 mL) and 2N aqueous HCl (5 mL). The solution was warmed to about 100° C. for about 3 h. The solution was allowed to cool to ambient temperature and the volatiles were removed under reduced pressure. The aqueous mixture was slurried in saturated aqueous NaHCO3/water (1:1, 100 mL) and DCM (50 mL). The solid was collected by filtration, rinsed with water and DCM, and dried to afford 3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-amine (0.343 g, 43%): LC/MS (Table 1, Method n) Rt=0.56 min; MS m/z: 328 (M+H)+.

Workup

  1. customa reflux condenser was attached
  2. waitAfter about 2 h
  3. temperatureto cool to ambient temperature
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 1,4-dioxane (5 mL)
  6. temperatureThe solution was warmed to about 100° C. for about 3 h
  7. temperatureto cool to ambient temperature
  8. customthe volatiles were removed under reduced pressure
  9. filtrationThe solid was collected by filtration
  10. washrinsed with water and DCM
  11. customdried

Sources & evidence

ORD record
ord-ee204b6163e74cda89b18bc09a4146a6
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…