Réaction #2186203

ord-521455caad8c415796162a02be19875e

Équation de réaction

O=Cc1ccc(N2CCN(CCF)CC2)cc1O
4-[4-(2-Fluoro-ethyl)-piperazin-1-yl]-2-hydroxy-benzaldehyde
COC(=O)Cc1cn2cc(Cl)ccc2n1
(6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester
CC#N
acetonitrile
C1CCNCC1
piperidine
O=c1oc2cc(N3CCN(CCF)CC3)ccc2cc1-c1cn2cc(Cl)ccc2n1
desired product
Rendement 23.4%
O=c1oc2cc(N3CCN(CCF)CC3)ccc2cc1-c1cn2cc(Cl)ccc2n1
3-(6-Chloro-imidazo[1,2-a]pyridin-2-yl)-7-[4-(2-fluoro-ethyl)-piperazin-1-yl]-chromen-2-one
Rendement 23.4%

Solvants

Conditions de réaction

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

Traitement

  1. 1
    Filtrationthe precipitated material filtered
  2. 2
    Lavagewashed with diethyl ether
  3. 3
    Autredried under high vacuum

Mode opératoire

253 mg (1 mmol) 4-[4-(2-Fluoro-ethyl)-piperazin-1-yl]-2-hydroxy-benzaldehyde and 450 mg (2 eq.) (6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester refluxed in 15 mL benzene and 7.5 mL acetonitrile in the presence of 0.395 mL (4 eq.) piperidine for 21 h. The reaction mixture is cooled to 0° C. and the precipitated material filtered, washed with diethyl ether and dried under high vacuum, yielding 100 mg (23%) desired product as a yellow solid. M.p.=265° C. (decomposition).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07569337B2uspto-grants-2009_08