2-Aminopyridine → HCID 13260278, compound

HRID 1649013Notes

Reaction equation

HRID 1649013 reaction equation
[Br:1][CH:2]([CH2:18][CH3:19])[C:3]([C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:17])[NH:10]2)=O.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1>C(#N)C>[BrH:1].[CH2:18]([C:2]1[N:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]2=[N:20][C:3]=1[C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:17])[NH:10]2)[CH3:19]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 13533239HCID 13533239, compound

Product 1

HCID 13260278HCID 13260278, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(α-bromobutyryl)-8-methoxy-3,4-dihydrocarbostyril (5 g), 2-aminopyridine (4.33 g) and acetonitrile (20 ml) were reacted by refluxing for 6 hours. The reaction mixture was concentrated to dryness and the residue was crystallized by the addition of water. The crystals were collected by filtration and washed with water. The crystals were dissolved in acetone and the solution was adjusted to pH of about 1 to 2 by the addition of 48% hydrobromic acid. Crystals which formed were collected by filtration. The crude crystals thus obtained were recrystallized from methanol-ether to give 3.73 g of 5-(3-ethylimidazo[1,2-a]pyridine-2-yl)-8-methoxy-3,4-dihydrocarbostyril monohydrobromide.

Workup

  1. temperatureby refluxing for 6 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customthe residue was crystallized by the addition of water
  4. filtrationThe crystals were collected by filtration
  5. washwashed with water
  6. dissolutionThe crystals were dissolved in acetone
  7. additionthe solution was adjusted to pH of about 1 to 2 by the addition of 48% hydrobromic acid
  8. customCrystals which formed
  9. filtrationwere collected by filtration
  10. customThe crude crystals thus obtained
  11. customwere recrystallized from methanol-ether

Sources & evidence

ORD record
ord-85b3cf18498343b8804ffa9d7e422fd2
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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