Sodium Hydroxide → 3-((2'-Carboxybiphenyl-4-yl)methyl)-2-cyclopropyl-7-methyl-3H-imidazo(4,5-b)pyridine

HRID 1940958Notes

Reaction equation

HRID 1940958 reaction equation
[OH-].[Na+].[CH:3]1([C:6]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([O:31]C)=[O:30])=[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>C(O)C>[CH:3]1([C:6]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:31])=[O:30])=[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

Participants

4

Reactant 2

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

Product 1

HCID 1318573-((2'-Carboxybiphenyl-4-yl)methyl)-2-cyclopropyl-7-methyl-3H-imidazo(4,5-b)pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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-5280ef1eedb34835844189eed144dbd0
Source dataset
uspto-grants-1997_12
Patent number
US05700938

Reaction notes

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