Reaktion #508771

ord-193f865f55d04c79be7d35619b62b944

Reaktionsgleichung

O[C@H]1CC[C@H](Nc2ncc3nc(Nc4c(F)cccc4F)n(C4CCCC4)c3n2)CC1
trans-4-(8-(2,6-Difluorophenylamino)-9-cyclopentyl-9H-purin-2-ylamino)cyclohexanol
O=C1CCC(=O)O1
succinic anhydride
→
O=C(O)CCC(=O)O[C@H]1CC[C@H](Nc2ncc3nc(Nc4c(F)cccc4F)n(C4CCCC4)c3n2)CC1
desired product
O=C(O)CCC(=O)O[C@H]1CC[C@H](Nc2ncc3nc(Nc4c(F)cccc4F)n(C4CCCC4)c3n2)CC1
3-((trans-4-(8-(2,6-Difluorophenylamino)-9-cyclopentyl-9H-purin-2-ylamino)cyclohexyloxy)carbonyl)propanoic acid

Edukte

O[C@H]1CC[C@H](Nc2ncc3nc(Nc4c(F)cccc4F)n(C4CCCC4)c3n2)CC1
trans-4-(8-(2,6-Difluorophenylamino)-9-cyclopentyl-9H-purin-2-ylamino)cyclohexanol
O=C1CCC(=O)O1
succinic anhydride

Reagenzien

Keine

Lösungsmittel

c1ccncc1
pyridine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture was heated at 50° C. for about 10 hours
  2. 2
    Sonstigethe solvent was subsequently evaporated
  3. 3
    SonstigeThe residue was recrystallized from acetone/MeOH

Vorschrift

trans-4-(8-(2,6-Difluorophenylamino)-9-cyclopentyl-9H-purin-2-ylamino)cyclohexanol (1 mmol, 1 eq.) and succinic anhydride (10 mmol, 10 eq.) were mixed in 25 mL pyridine and stirred at room temperature for 3 days. The mixture was heated at 50° C. for about 10 hours and the solvent was subsequently evaporated. The residue was recrystallized from acetone/MeOH to give the desired product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08101588B2uspto-grants-2012_01