Potassium Hydroxide → HCID 23720483, compound

HRID 2351674Notes

Reaction equation

HRID 2351674 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:27])[CH2:10][N:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[N:13]=[C:12]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)C.[OH-].[K+:30]>C(O)C>[OH2:3].[K+:30].[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:12]2[N:11]([CH2:10][C:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4]([O-:28])=[O:3])=[O:27])[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[N:13]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14390244HCID 14390244, compound

Product 1

HCID 23720483HCID 23720483, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[[[2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridin-3-yl]acetyl]amino]butanoic acid ethyl ester (3.3 g, 0.008 mole), potassium hydroxide (0.5 g, 0.009 mole), and 80 ml of 95% ethyl alcohol was heated at reflux for 13/4 hours. The hot reaction mixture was filtered, washed with absolute ethanol, and the filtrate was evaporated to a solid residue. The solid was triturated with acetone and filtered. The solid was dissolved in hot tert-butanol and allowed to cool with seeding. The crystalline precipitate was collected by filtration, washed with tert-butyl alcohol and dried under high vacuum at 50° C. overnight to give 1.2 g (35%) of title compound, mp 263°-264° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 13/4 hours
  3. filtrationThe hot reaction mixture was filtered
  4. washwashed with absolute ethanol
  5. customthe filtrate was evaporated to a solid residue
  6. customThe solid was triturated with acetone
  7. filtrationfiltered
  8. dissolutionThe solid was dissolved in hot tert-butanol
  9. temperatureto cool with seeding
  10. filtrationThe crystalline precipitate was collected by filtration
  11. washwashed with tert-butyl alcohol
  12. customdried under high vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-a437916de77f4556be4ce973d1afb000
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

Loading…