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

HRID 564491Notes

Reaction equation

HRID 564491 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].[OH-].[Li+].C1COCC1.Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 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 Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (0.706 g, 1.518 mmol), lithium hydroxide (0.0545 g, 2.28 mmol), THF (60 mL), and water (20 mL) were combined and stirred under argon at room temperature overnight. Solvents were pumped off, and the residue taken up in water (20 mL). The mixture was acidified with HCl until it appeared that no more precipitate was forming. The pH at this time was about 6. The solid was filtered off and washed 2× with a small volume of water. The material was dried under vacuum for two days until weight loss was minimal to give the title compound as a white solid. LC-MS m/z 451.8 (M+H)+, 1.48 min (ret time); mp 207-209° C.; analytical HPLC shows 100% purity, (ret time 10.177 min).

Workup

  1. customwas forming
  2. filtrationThe solid was filtered off
  3. washwashed 2× with a small volume of water
  4. customThe material was dried under vacuum for two days until weight loss

Sources & evidence

ORD record
ord-5dba60f760b341e3998b78fb11dad899
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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