Water → HCID 57975835, compound

HRID 2388998Notes

Reaction equation

HRID 2388998 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:42])[C:6]1[CH:16]=[C:15]([C:17]2[CH:18]=[C:19]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[N:24][N:23]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:20]3=[N:21][CH:22]=2)[CH:14]=[C:8]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:7]=1.O>O.CO>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]1[C:19]2[C:20](=[N:21][CH:22]=[C:17]([C:15]3[CH:14]=[C:8]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:7]=[C:6]([CH:16]=3)[C:5]([OH:42])=[O:4])[CH:18]=2)[N:23]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:39])[CH3:40])[N:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57975871HCID 57975871, compound

Product 1

HCID 57975835HCID 57975835, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

4 N aqueous lithium hydroxide (0.43 ml, 1.71 mmol) was added to 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-isophthalamic acid methyl ester (0.80 g, 1.43 mmol) in water/methanol (3:1) and stirred at room temperature for 16 hours, water was added and the mixture was extracted with ethyl acetate (3×), the combined organic layers were dried over magnesium sulfate and purified by silica gel chromatography to give 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-isophthalamic acid (717 mg, 92% yield) of an off white powder. MS: m/z 546.7 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. dry with materialthe combined organic layers were dried over magnesium sulfate
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6c7b855d48ff4b008b9e30d4632c96cd
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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