Reaktion #1269848

ord-44f52011ce894f968b2a8a979f922d45

Reaktionsgleichung

CN1C(=O)c2cn(Cc3ccc(-c4cccc(F)n4)cc3)c(Cl)c2N2C1=N[C@@H]1CCC[C@@H]12
(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-1-chloro-5-methyl-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one
O=C(O)C(Cl)(Cl)Cl
trichloroacetic acid
Nc1ccccc1
aniline
CN1C(=O)c2cn(Cc3ccc(-c4cccc(F)n4)cc3)c(Nc3ccccc3)c2N2C1=N[C@@H]1CCC[C@@H]12
product
Ausbeute 14.5%
CN1C(=O)c2cn(Cc3ccc(-c4cccc(F)n4)cc3)c(Nc3ccccc3)c2N2C1=N[C@@H]1CCC[C@@H]12
(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-1-(phenylamino)-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one
Ausbeute 14.5%

Lösungsmittel

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe mixture is purified by a semi-preparative HPLC

Vorschrift

Crude (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-1-chloro-5-methyl-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one (approx. 0.03 mmol) is dissolved in anhydrous CH2Cl2, and then trichloroacetic acid (5.2 mg, 0.03 mmol) is added, followed by aniline (5.8 uL, 0.06 mmol). The reaction mixture is heated in a Biotage microwave instrument at 100° C. for 2 hours. The mixture is purified by a semi-preparative HPLC to give 2.2 mg of product as solids. MS (ESI) m/z 507.2 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08664207B2uspto-grants-2014_03