Sodium Hydroxide → 4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol

HRID 2283851Notes

Reaction equation

HRID 2283851 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:34][CH2:35][CH3:36])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[N:19](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.[OH-].[Na+]>Cl.C(O)C.CO>[NH2:19][C:10]1[C:9]2=[N:8][N:7]([CH2:34][CH2:35][CH3:36])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[C:18]2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66958564di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate

Product 1

HCID 577175804-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-olYield 27.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate (prepared as described in Parts A-C of Example 57, 0.507 g, 1.02 mmol) in 6 M HCl in ethanol (5 mL) was heated at 60° C. for 1.5 hours. The solution was allowed to cool to room temperature, and then was concentrated under reduced pressure to yield an oil. The oil was triturated with ether to obtain a solid that was isolated by filtration. The solid was dissolved in methanol and the solution was adjusted to approximately pH 14 with 50% aqueous sodium hydroxide. The solution was concentrated under reduced pressure and the crude product was purified by chromatography (silica gel, elution with 5% CMA in chloroform) followed by crystallization from hexanes/ethyl acetate to provide 0.084 g of 4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol as white needles, mp 135.0-136.0° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an oil
  3. customThe oil was triturated with ether
  4. customto obtain a solid
  5. customthat was isolated by filtration
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe crude product was purified by chromatography (silica gel, elution with 5% CMA in chloroform)
  8. customfollowed by crystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-15ca692c9fd34daca9636500b60cdb81
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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