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Water → 4-{(3S)-3-[(tert-Butoxycarbonyl)amino]piperidin-1-yl}-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 1499482
Notes
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Reaction equation

HRID 1499482 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][N:21]=[C:20]3[N:29]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[N:30]=[CH:31][C:19]=23)[CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>CO.C1COCC1>[C:4]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=[C:20]3[N:29]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[N:30]=[CH:31][C:19]=23)[CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86726715HCID 86726715, compound

Product 1

HCID 867267164-{(3S)-3-[(tert-Butoxycarbonyl)amino]piperidin-1-yl}-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

Water (5 mL) and lithium hydroxide (1.5 g, 63 mmol) were added to a solution of ethyl 4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.9 g, 3.7 mmol) in MeOH (5 mL) and THF (5 mL). The mixture heated at 50° C. with stirring for 2 h. The mixture was allowed to cool to room and concentrated under reduced pressure. The residue was neutralized with 2N HCl and extracted twice with EtOAc. The organic extract was dried with Na2SO4 and concentrated under reduced pressure to give the sub-title compound (1.6 g (89%). LCMS calc. for C25H32N5O5 (M+H)+: m/z=482.2. Found: 482.1.

Workup

  1. temperatureto cool to room
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted twice with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried with Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e23c7cca575d435195510663a8aecf7f
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09200004B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes