Réaction #1269847

ord-a19285ed96974da2939911290f36a9f0

Équation de réaction

CN1C(=O)c2cn(Cc3ccc(-c4cccc(F)n4)cc3)cc2N2C1=N[C@@H]1CCC[C@@H]12
(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-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=C1CCC(=O)N1Cl
N-chlorosuccinimide
→
CN1C(=O)c2cn(Cc3ccc(-c4cccc(F)n4)cc3)c(Cl)c2N2C1=N[C@@H]1CCC[C@@H]12
solids
Rendement 45.0%
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
Rendement 45.0%

Réactifs

CN1C(=O)c2cn(Cc3ccc(-c4cccc(F)n4)cc3)cc2N2C1=N[C@@H]1CCC[C@@H]12
(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-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=C1CCC(=O)N1Cl
N-chlorosuccinimide

Réactifs

Aucun

Solvants

ClC(Cl)(Cl)Cl
CCl4
CN(C)C=O
DMF
ClC(Cl)(Cl)Cl
CCl4
CN(C)C=O
DMF

Conditions de réaction

Température
0°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreSolvents are removed under vacuum
  2. 2
    Autrethe residue is purified by a semi-preparative HPLC

Mode opératoire

(6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-2-(4-(6-fluoropyridin-2-yl)benzyl)-cyclopent[4,5]imidazo[1,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one (38 mg, 0.082 mmol) is dissolved in a mixture of CCl4 and DMF (8/1, v/v). The solution is cooled to 0° C., and then a solution of N-chlorosuccinimide (10.9 mg, 0.082 mmol) in CCl4 and DMF (8/1, v/v) is added dropwise. The reaction mixture is stirred at room temperature for half an hour. Solvents are removed under vacuum, and the residue is purified by a semi-preparative HPLC to give pure product as off white solids (16.5 mg, yield 45%). MS (ESI) m/z 450.1 [M+H]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08664207B2uspto-grants-2014_03