Sodium Hydroxide → [4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamino]-phenyl-acetic acid
Reaction equation
[C:1]([CH:5]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]2[C:24]3=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]3[N:22]=[C:21]2[CH2:31][CH3:32])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([CH:5]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][N:20]2[C:24]3=[N:25][C:26]([CH3:30])=[CH:27][C:28]([CH3:29])=[C:23]3[N:22]=[C:21]2[CH2:31][CH3:32])=[CH:17][CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([OH:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.45 g of the product of Step A dissolved in 5.0 mL methanol, was added 3.0 mL of 3N NaOH solution, and the mixture was stirred for 30 minutes. The methanol was removed in vacuo and the water was removed by azeotropic distillation with toluene. The o toluene was removed in vacuo, then the product was redissolved in CHCl3 and excess NaOH was removed by filtration of the suspension through a celite pad. The filtrate was concentrated to a clear oil and purified on a silica gel flash chromatography column eluted with CHCl3 /MeOH/NH4OH (80:15:1). The product fractions were combined and concentrated. The resultant oil was triturated with ether to yield 396 mg (91%) of the title compound as a white powder.