Sodium Hydroxide → HCID 10287414, compound
Reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][CH2:27][O:28][CH3:29])[CH:18]=3)[CH2:13][CH2:12]2)[CH:5]=1.[OH-].[Na+]>C(O)C>[CH3:29][O:28][CH2:27][CH2:26][N:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([CH:14]2[CH2:15][CH2:16][N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])[CH2:12][CH2:13]2)=[CH:18]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.66 g (1.62 mmol) of 3-{4-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidin-1-ylmethyl}-benzoic acid methyl ester were dissolved in 0.8 ml of ethyl alcohol and 2.43 ml of 2 N sodium hydroxide were added. After stirring at room temperature for 20 hours, the solvent was evaporated under reduced pressure and the residue dissolved in water. The mixture was neutralised with 2 N hydrochloric acid and extracted twice with dichlormethane. The organic phase was washed with water and brine, dried with magnesium sulphate, filtrated and evaporated. The crude material weighed 0.46 g and was purified by flash chromatography over silica gel affording 0.2 g (31% of yield) of the expected product.