反应详情

A mixture of 2.7 parts of a sodium hydride dispersion 50% and 282 parts of N,N-dimethylformamide was stirred at room temperature under nitrogen atmosphere. 18.8 Parts of ethyl 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate were added portionwise to the previous mixture. Upon complete addition, stirring for continued for 1 hour at room temperature. 10 Parts of (bromomethyl)benzene were added dropwise and upon completion, stirring was continued for 1 hour. The reaction mixture was decomposed with water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and ethanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.2 parts (13.6%) of ethyl 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b] pyridin-2-yl](phenylmethyl)amino]-1-piperidinecarboxylate; mp. 115.0° C. (compound 177).

1. additionUpon complete addition
2. stirringstirring
3. stirringstirring
4. waitwas continued for 1 hour
5. extractionthe product was extracted with 4-methyl-2-pentanone
6. customThe extract was dried
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by column chromatography over silica gel using
10. additiona mixture of trichloromethane and ethanol (98:2 by volume) as eluent
11. customThe pure fractions were collected
12. customthe eluent was evaporated
13. customThe residue was crystallized from 2,2'-oxybispropane
14. filtrationThe product was filtered off
15. customdried