Ethanol → HCID 19422670, compound

HRID 744982Notes

Reaction equation

HRID 744982 reaction equation
[OH-:1].[Na+].[CH:3]1([C:6]2[N:15]([CH2:16][C:17]3[CH:22]=C[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4C(OC)=O)=[CH:19][CH:18]=3)[C:9]3=[N:10][CH:11]=[CH:12][C:13]([CH3:14])=[C:8]3[N:7]=2)[CH2:5][CH2:4]1.[CH2:33]([OH:35])[CH3:34]>>[CH:3]1([C:6]2[N:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:34]([C:33]([OH:1])=[O:35])[CH:22]=3)[C:9]3=[N:10][CH:11]=[CH:12][C:13]([CH3:14])=[C:8]3[N:7]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 110367292-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 19422670HCID 19422670, compoundYield 81%

Procedure

Ethanol (40 ml) and a 10% aqueous solution (20 ml) of sodium hydroxide were added to 1.32 g (3.3 mmol) of 2-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine, followed by heating under reflux for 2 hours. After the reaction liquid was cooled, it was concentrated to about one-half the initial volume, and neutralized with 2N hydrochloric acid and acetic acid. The crystal thus precipitated was recovered by filtration and recrystallized from aqueous ethanol to give 1.03 of the title compound (yield 81%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. customAfter the reaction liquid
  4. temperaturewas cooled
  5. concentrationit was concentrated to about one-half the initial volume
  6. customThe crystal thus precipitated
  7. filtrationwas recovered by filtration
  8. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-49c7ed8086134e7990a06ea72a5c9410
Source dataset
uspto-grants-1996_09
Patent number
US05559236

Reaction notes

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