benzyl 1-oxo-2-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate → 2-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1775097Notes

Reaction equation

HRID 1775097 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9](C(OCC3C=CC=CC=3)=O)[CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]1[C:22]1[C:30]2[C:25](=[CH:26][N:27]=[C:28]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:29]=2)[N:24](COCC[Si](C)(C)C)[N:23]=1>Cl.O>[N:33]1[CH:34]=[CH:35][CH:36]=[C:31]([C:28]2[CH:29]=[C:30]3[C:22]([N:3]4[CH2:4][CH2:5][C:6]5([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]5)[C:2]4=[O:1])=[N:23][NH:24][C:25]3=[CH:26][N:27]=2)[CH:32]=1

Participants

4

Reactant 1

HCID 71253852benzyl 1-oxo-2-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 712539922-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decan-1-oneYield 26.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of benzyl 1-oxo-2-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (0.140 g, 0.229 mmol) in 2.00 M of Hydrogen chloride in Water (16.2 mL) was stirred at 100° C. for 18 h. The reaction was concentrated then submitted for rHPLC to give 295 (21.2 mg, 26.5% yield). ESI MS m/z=349.2 (M+1). 1H NMR (400 MHz, DMSO) δ 9.19 (d, J=1.8 Hz, 1H), 9.07 (s, 1H), 8.67 (s, 1H), 8.57 (d, J=4.6 Hz, 1H), 8.33 (d, J=8.0 Hz, 1H), 7.51 (dd, J=7.9, 4.7 Hz, 1H), 3.97 (t, J=7.0 Hz, 2H), 2.92 (d, J=12.6 Hz, 2H), 2.63 (dd, J=21.4, 9.3 Hz, 2H), 2.20 (t, J=7.0 Hz, 2H), 1.74 (td, J=12.5, 4.1 Hz, 2H), 1.48 (d, J=13.0 Hz, 2H)

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-c45be88ea0514cf1901a537cd4037b37
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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