Hydrochloric Acid → 2'-isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochloride

HRID 711033Notes

Reaction equation

HRID 711033 reaction equation
[CH:1]([N:4]1[CH:12]=[C:11]2[C:6]([C:7](=[O:25])[NH:8][C:9]3([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH2:10]2)=[N:5]1)([CH3:3])[CH3:2].[ClH:26]>C(OCC)(=O)C.O1CCOCC1>[ClH:26].[CH:1]([N:4]1[CH:12]=[C:11]2[C:6]([C:7](=[O:25])[NH:8][C:9]3([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[CH2:10]2)=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67491432Tert-butyl 2'-isopropyl-7'-oxo-2',4',6',7'-tetrahydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridine]-1-carboxylate

Product 1

HCID 674915642'-isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one hydrochloride

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2′-isopropyl-7′-oxo-2′,4′,6′,7′-tetrahydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridine]-1-carboxylate (130 mg, 0.37 mmol) in ethyl acetate (5 mL) was added 4 M hydrochloric acid (2 mL) in 1,4-dioxane. The reaction mixture was stirred 3 hours at room temperature, the volatiles were removed under reduced pressure and the resultant residue was triturated with 10 mL heptane. The solid was dried under reduced pressure to yield 2′-isopropyl-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(2′H)-one hydrochloride (105 mg) as an off-white solid. +ESI (M+H) 249.1; 1H NMR (500 MHz, DMSO-d6, δ): 7.91 (s, 1H) 7.69 (s, 1H) 4.48-4.62 (m, 1H) 3.02-3.28 (m, 4H) 2.78 (s, 2H) 1.74-1.89 (m, 4H) 1.41 (d, J=6.59 Hz, 6H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe resultant residue was triturated with 10 mL heptane
  3. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-be846f8eb3ad4c5f842afd2e738becca
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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