Ethanol → HCID 131716478, compound

HRID 2166141Notes

Reaction equation

HRID 2166141 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][CH2:11][CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][NH2:31])[CH2:25][CH2:24]1)[CH3:9].[C:32](=[O:35])([O-:34])O.[Na+].C([OH:39])C>>[C:11]([OH:10])(=[O:39])[C:32]([OH:34])=[O:35].[CH2:8]([O:10][CH2:11][CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:22][CH:23]1[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][NH:31][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:27][CH2:28]1)[CH3:9]

Participants

5

Reactant 4

HCID 702EthanolHCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 15718932HCID 15718932, compound

Product 1

HCID 131716478HCID 131716478, compoundYield 48.7%

Procedure

A mixture of 1.7 parts of 2-chloropyrimidine, 4.33 parts of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidineethanamine, 1.7 parts of sodium hydrogen carbonate and 40 parts of ethanol was stirred overnight at reflux temperature. The reaction mixture was evaporated and the residue was poured into water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in a mixture of ethanol and 2-propanone. The salt was filtered off and dried, yielding 4.97 parts (48.7%) of N-[2-[4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperidinyl]ethyl]-2-pyrimidinamine ethanedioate(1:3); mp. 119.7° C. (compound 131).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionthe residue was poured into water
  4. extractionThe product was extracted with trichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. additionThe residue was converted into the ethanedioate salt in a mixture of ethanol and 2-propanone
  13. filtrationThe salt was filtered off
  14. customdried

Sources & evidence

ORD record
ord-a516a644cd1f478d99669cf6b00af4ed
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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