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

HRID 1499482Notes

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]

Participants

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

temperatureto cool to room
concentrationconcentrated under reduced pressure
extractionextracted twice with EtOAc
extractionThe organic extract
dry with materialwas dried with Na2SO4
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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