Sodium Hydroxide → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 2279139Notes

Reaction equation

HRID 2279139 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[C:24]([CH3:25])=[N:23][N:22]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:8]=2[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][O:20][CH3:21])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:21][O:20][CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]3[C:24]([CH3:25])=[N:23][N:22]([CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][O:27]4)[C:8]=3[N:9]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 900137956-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Product 1

HCID 900138076-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.09 g 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester in 140 ml ethanol was added 100 ml of 1M aqueous sodium hydroxide solution. After 3 h at r.t. the volatiles were removed in vacuo. The residue was taken up in water and the pH was adjusted to 4-5. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, dichloromethane/MeOH gradient with addition of aqueous ammonia) to obtain 1.74 g (90%) of the title compound.

Workup

  1. customAfter 3 h at r.t. the volatiles were removed in vacuo
  2. extractionThe aqueous phase was extracted with ethyl acetate three times
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, dichloromethane/MeOH gradient with addition of aqueous ammonia)

Sources & evidence

ORD record
ord-fc42d8a68d8d43238dd7a9b18b80da58
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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