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

HRID 657388Notes

Reaction equation

HRID 657388 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:30][CH3:31])=[C:10]([CH2:19][NH:20][C:21](=[O:29])[CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])[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].O[Li].O.Cl>CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:30][CH3:31])=[C:10]([CH2:19][NH:20][C:21](=[O:29])[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57819898Methyl 5-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-5-oxopentanoate

Product 1

HCID 578198975-({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-5-oxopentanoic AcidYield 82.84%

Reagents, catalysts & solvents 1

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

Procedure

To methyl 5-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-5-oxopentanoate (0.450 g, 1.043 mmol) in MeOH/H2O was added LiOH.H2O and stirred at room temperature for 16 h. The mixture was the acidified with HCl (1 N) and extracted with DCM/i-PrOH (3/1) which was dried over Na2SO4 and concentrated to afford the title compound (0.3606 g, 82.84%). LC-MS m/z 418 (M+H)+.

Workup

  1. extractionextracted with DCM/i-PrOH (3/1) which
  2. dry with materialwas dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b4753a6b713848d79c89f914c0be8288
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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