Lithium Hydroxide → 3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

HRID 564560Notes

Reaction equation

HRID 564560 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:33][CH3:34])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=3)[C:26]([O:28]C)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[Li+].[OH-]>CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:33][CH3:34])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=3)[C:26]([OH:28])=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57813262Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate

Product 1

HCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic AcidYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (3.51 g, 7.54 mmol) in methanol (22.6 mL) and water (11.30 mL), was added LiOH.H20 (1.582 g, 37.7 mmol). This was stirred at room temperature for 19 h. MeOH was removed under vacuo. The aqueous layer was acidified with HCl (1 N) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to afford the title compound (2.2082 g, 65%). LC-MS m/z 452 (M+H)+.

Workup

  1. customMeOH was removed under vacuo
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cee9cb6968c94478aac17ef619099cc6
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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