Hydrochloric Acid → 1'-isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-one

HRID 880896Notes

Reaction equation

HRID 880896 reaction equation
[CH:1]([N:4]1[C:8]2[C:9](=[O:25])[NH:10][C:11]3([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH2:12][C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2].Cl.CO>C(OCC)(=O)C.O1CCOCC1>[CH:1]([N:4]1[C:8]2[C:9](=[O:25])[NH:10][C:11]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:12][C:7]=2[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67491663Tert-butyl 1'-isopropyl-7'-oxo-1',4',6',7'-tetrahydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridine]-1-carboxylate

Product 1

HCID 674915361'-isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-oneYield 98.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 1′-isopropyl-7′-oxo-1′,4′,6′,7′-tetrahydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridine]-1-carboxylate (100 mg, 0.29 mmol) in 4 mL ethyl acetate was added 4 N HCl in dioxane (2 mL). After stirring 30 minutes at room temperature, methanol (1 mL) was added and the resultant solution was stirred for 5 hours at room temperature. The volatiles were removed under reduced pressure and the resultant colorless solid triturated with 1:1 acetonitrile/dichloromethane to yield 71 mg of the title compound as a colorless solid. 1H NMR (400 MHz, DMSO-d6, δ): 8.72 (br. s., 2H), 8.05 (s, 1H), 7.37 (s, 1H), 5.36 (m, 1H), 3.15 (m, 2H), 3.05 (m, 2H), 2.78 (s, 2H), 1.78 (m, 4H), 1.33 (d, J=6.6 Hz, 6H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resultant colorless solid triturated with 1:1 acetonitrile/dichloromethane

Sources & evidence

ORD record
ord-0c05ad45aebe4fc7a2910b5ab3aca505
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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