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

HRID 975310Notes

Reaction equation

HRID 975310 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%). 1H-NMR (600 MHz, DMSO-d6); δ (ppm) 1.06 (4H, m), 2.27 (1H, tt, J=8.0, 5.0 Hz), 2.50 (3H, s), 5.63 (2H, s), 7.04 (1H, d, J=5.0 Hz), 7.27 (4H, m), 7.33 (1H, dd, J=8.0, 1.0 Hz), 7.43 (1H, ddd, J=8.0, 8.0, 1.0 Hz), 7.54 (1H, ddd, J=8.0, 8.0, 2.0 Hz), 7.70 (1H, dd, J=8.0, 2.0 Hz), 8.13 (1H, d, J=5.0 Hz), 12.70 (1H, br-s)

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-6a51163ab2054437bd8f350b00c0a100
Source dataset
uspto-grants-1997_03
Patent number
US05608068

Reaction notes

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