Potassium Hydroxide → HCID 57717500, compound

HRID 1360533Notes

Reaction equation

HRID 1360533 reaction equation
[CH2:1]([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)[CH2:2][CH2:3][C:4]#[CH:5].[OH-].[K+]>Cl.C(O)C>[CH2:1]([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[NH2:19])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86604924HCID 86604924, compound

Product 1

HCID 57717500HCID 57717500, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of di(tert-butyl) 1-pent-4-ynyl-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate (prepared as described in Parts A-E of Example 57, 0.400 g, 0.812 mmol) in 6 M HCl in ethanol (3 mL) was heated at 60° C. for 1.7 hours. The solution was allowed to cool to room temperature, and then was concentrated under reduced pressure to yield an oil. The oil was treated with 1 M aqueous potassium hydroxide to generate a white precipitate, which was isolated by filtration. The crude product was purified by chromatography (silica gel, gradient elution with 5-10% CMA in chloroform) followed by crystallization from hexanes/ethyl acetate to afford 0.061 g of 1-pent-4-ynyl-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine as white crystals, mp 144.0-145.0° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an oil
  3. customwhich was isolated by filtration
  4. customThe crude product was purified by chromatography (silica gel, gradient elution with 5-10% CMA in chloroform)
  5. customfollowed by crystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2b8ead45e8ec4f758fb1eb955e1c07b1
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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