Reacción #1269848

ord-44f52011ce894f968b2a8a979f922d45

Ecuación de reacción

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
Rendimiento 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
Rendimiento 14.5%

Disolventes

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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]+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08664207B2uspto-grants-2014_03