Hydrochloric Acid → 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acid

HRID 657378Notes

Reaction equation

HRID 657378 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:29][CH3:30])=[C:10]([CH2:19][NH:20][C:21](=[O:28])[CH2:22][C:23]([O:25]CC)=[O:24])[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-].O.Cl>[Cl-].[Na+].O.C(O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:29][CH3:30])=[C:10]([CH2:19][NH:20][C:21](=[O:28])[CH2:22][C:23]([OH:25])=[O:24])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 57819880ethyl 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoate

Product 1

HCID 578198663-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acidYield 75.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of ethyl 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoate (130 mg, 0.30 mmol), LiOH (63 mg, 1.5 mmol), water (1 mL) and ethanol (2 mL) was stirred at room temperature overnight. The aqueous layer was acidified with 2 N HCl to PH<1. Brine (30 mL) was added to the solution. The aqueous layer was extracted with a mixture of DCM:IPA (4:1) twice. The organic layer was dried over sodium sulfate, filtered and then concentrated under vacuum to give 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acid (88 mg, 75%). LC-MS m/z 390 (M+H)+.

Workup

  1. extractionThe aqueous layer was extracted with a mixture of DCM:IPA (4:1) twice
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2e67d7da83d34dcbb7b39ca10e5cd15f
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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