Allyl bromide → HCID 131716288, compound

HRID 330545Notes

Reaction equation

HRID 330545 reaction equation
Br[CH2:2][CH:3]=[CH2:4].[C:5](O)(=O)[C:6]([OH:8])=[O:7].[CH3:11][C:12]1[O:16][C:15]([CH2:17][N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[N:20]=[C:19]2[NH:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:14][CH:13]=1.C(=O)([O-])[OH:35].[Na+]>C(O)C>[C:15]([OH:35])(=[O:16])/[CH:17]=[CH:5]/[C:6]([OH:8])=[O:7].[CH3:11][C:12]1[O:16][C:15]([CH2:17][N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[N:20]=[C:19]2[NH:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:4][CH:3]=[CH2:2])[CH2:30][CH2:29]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 86743720HCID 86743720, compound

Product 1

HCID 131716288HCID 131716288, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.82 parts of 3-bromo-1-propene, 7.4 parts of 3-[(5-methyl-2-furanyl)methyl]-N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amine ethanedioate (2:1), 4.2 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred overnight at reflux temperature. The reaction mixture was filtered and the filtrate was evaporated. The residue was taken up in water and 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 (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in a mixture of 2-propanone and methanol. The salt was filtered off and dried, yielding 2 parts (23%) of 3-[(5-methyl-2-furanyl)methyl]-N-[1-(2-propenyl)-4-piperidinyl]-3H-imidazo-[4,5-b]pyridin-2-amine (E)-2-butenedioate(1:2); mp. 172.7° C. (compound 5).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  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 (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. additionThe residue was converted into the (E)-2-butenedioate salt in a mixture of 2-propanone and methanol
  13. filtrationThe salt was filtered off
  14. customdried

Sources & evidence

ORD record
ord-ae259e3917b140baa249dc24c66b56fd
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

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