Water → HCID 178526024, compound

HRID 1904834Notes

Reaction equation

HRID 1904834 reaction equation
Cl.Cl.FC1C=CC(C[N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=[C:12]2CC2CCNCC2)=CC=1.[C:27](=[O:30])([O-:29])[O-].[Na+].[Na+].CC(C)C[C:36](=[O:38])C.C(C1C=CC=CN=1)=C.[OH2:48]>>[C:36]([OH:38])(=[O:48])[C:27]([OH:29])=[O:30].[N:13]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[NH:11][CH:12]=1

Participants

6

Reactant 5

HCID 962Water3×HCID 75212-Vinylpyridine2×HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 20037917HCID 20037917, compound

Product 1

HCID 178526024HCID 178526024, compound

Procedure

A mixture of 7.9 parts of 3-[(4-fluorophenyl)methyl]-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridine dihydrochloride, 5.3 parts of sodium carbonate and 120 parts of 4-methyl-2-pentanone was stirred and refluxed for 15 minutes using a water separator. 3.2 Parts of 2-ethenylpyridine were added at reflux temperature and stirring was continued for 3 hours at reflux using a water separator. Then there were added 3.2 parts of 2-ethenylpyridine and the whole was stirred and refluxed for 19.50 hours using a water separator. After cooling, the salts were filtered off and the filtrate was washed with water, dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanone. The salt was filtered off and crystallized from a mixture of ethanol and 2-propanone, yielding 2.5 parts (17%) of 3-[(4-fluorophenyl)methyl]-2-[[1-[2-pyridinyl)ethyl]-4-piperidinyl]methyl]-3H-imidazo[4,5-b]-pyridine ethanedioate (1:3 ); mp. 143.1° C. (101).

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperatureat reflux temperature
  3. stirringstirring
  4. temperatureat reflux
  5. stirringthe whole was stirred
  6. temperaturerefluxed for 19.50 hours
  7. temperatureAfter cooling
  8. filtrationthe salts were filtered off
  9. washthe filtrate was washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. filtrationThe salt was filtered off
  14. customcrystallized from a mixture of ethanol and 2-propanone

Sources & evidence

ORD record
ord-8e47bb3593cf46d1a330ccf67440bef0
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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