Sodium t-butoxide → HCID 57717593, compound

HRID 1984377Notes

Reaction equation

HRID 1984377 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:8]=[C:7]([C:14]#[N:15])[C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22]C(=O)C(C)(C)C)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[Na+]>C(O)C>[CH2:1]([C:5]1[N:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[N:8]=[C:7]2[C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[C:14]2[NH2:15])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 66959030HCID 66959030, compound

Product 1

HCID 57717593HCID 57717593, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[2-(5-butyl-1-tert-butyl-3-cyano-1H-pyrazol4-yl)phenyl]-2,2-dimethylpropanamide (1.63 g, 4.28 mmol) in ethanol was added sodium tert-butoxide (0.494 g, 5.14 mmol). The solution was heated at reflux for 1 day, then was allowed to cool to ambient temperature. A precipitate formed that was isolated by filtration and washed with a small amount of water (24 mL) and ethanol (3 ML) to yield 0.4667 g of 1-butyl-2-tert-butyl-2H-pyrazolo[3,4-c]quinolin-4-amine as off-white crystals, mp 222.0-223.0° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1 day
  3. customA precipitate formed
  4. customthat was isolated by filtration
  5. washwashed with a small amount of water (24 mL) and ethanol (3 ML)

Sources & evidence

ORD record
ord-dbe0cda273c74e54b9b4ab42b12d70c3
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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