Water → HCID 131715262, compound

HRID 2309631Notes

Reaction equation

HRID 2309631 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=[C:12]2[CH2:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1.[C:27](=[O:30])([O-:29])[O-].[Na+].[Na+].CC(C)C[C:36](=[O:38])C.[CH:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1)=[CH2:41].[OH2:48]>>[C:36]([OH:38])(=[O:48])[C:27]([OH:29])=[O:30].[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=[C:12]2[CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:41][CH2:40][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[CH2:23][CH2:22]2)=[CH:8][CH:9]=1

Participants

6

Reactant 5

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

Product 1

HCID 131715262HCID 131715262, compoundYield 17%

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-ethenylpyidine 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-propananone. 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-(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. addition3.2 Parts of 2-ethenylpyidine were added
  3. temperatureat reflux temperature
  4. stirringstirring
  5. temperatureat reflux
  6. stirringthe whole was stirred
  7. temperaturerefluxed for 19.50 hours
  8. temperatureAfter cooling
  9. filtrationthe salts were filtered off
  10. washthe filtrate was washed with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. filtrationThe salt was filtered off
  15. customcrystallized from a mixture of ethanol and 2-propanone

Sources & evidence

ORD record
ord-0db9c1fd39284f1598e12e606af5d29c
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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