Sodium ethoxide → HCID 57717522, compound

HRID 2283833Notes

Reaction equation

HRID 2283833 reaction equation
[O-]CC.[Na+].[C:5]([C:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[NH:20]C(=O)C(C)(C)C)=[C:10]([CH2:27][CH3:28])[N:9]([CH2:29][CH3:30])[N:8]=1)#[N:6]>C(O)C>[CH2:27]([C:10]1[N:9]([CH2:29][CH3:30])[N:8]=[C:7]2[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[N:20]=[C:5]2[NH2:6])[CH3:28]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 66958637HCID 66958637, compound

Product 1

HCID 57717522HCID 57717522, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium ethoxide in ethanol (21% by weight, 2.29 mL, 13.9 mmol) was added to a solution of N-[2-(3-cyano-1,5-diethyl-1H-pyrazol-4-yl)-5-methoxyphenyl]-2,2-dimethylpropanamide (0.5 g, 1.41 mmol) in ethanol (10 mL). The reaction mixture was stirred at room temperature for 20 minutes and then heated at reflux overnight. The reaction mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting residue was triturated with water to provide a solid that was isolated by filtration, washed with water, and dried. The material was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-20% CMA in chloroform) followed by crystallization from acetonitrile to yield 0.23 g of 1,2-diethyl-7-methoxy-2H-pyrazolo[3,4-c]quinolin-4-amine as beige needles, mp 210-211° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureto cool to room temperature
  4. concentrationwas concentrated under reduced pressure
  5. customThe resulting residue was triturated with water
  6. customto provide a solid
  7. customthat was isolated by filtration
  8. washwashed with water
  9. customdried
  10. customThe material was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-20% CMA in chloroform)
  11. customfollowed by crystallization from acetonitrile

Sources & evidence

ORD record
ord-1902df2455d64a41b88d0cb75ed4222f
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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