Dimethylamine → HCID 14822490, compound

HRID 2073781Notes

Reaction equation

HRID 2073781 reaction equation
[CH3:1][NH:2][CH3:3].[NH2:4][C:5]1[C:17]2[C:8](=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:18][CH3:19])=[CH:12][CH:11]=3)[N:7]([CH2:20][C:21]([O:23]CC)=O)[N:6]=1>CO>[NH2:4][C:5]1[C:17]2[C:8](=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:18][CH3:19])=[CH:12][CH:11]=3)[N:7]([CH2:20][C:21]([N:2]([CH3:3])[CH3:1])=[O:23])[N:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 14822485HCID 14822485, compound

Product 1

HCID 14822490HCID 14822490, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a saturated solution of dimethylamine in 250 ml methanol at 0° C. was added 4.5 g ethyl 3-amino-6-methoxy-1H-pyrazolo[3,4-b]quinolin-1-acetate (Example 20), and the mixture was stirred at 0° C. for one hour, at room temperature for 48 hours and at reflux for two hours. The reaction mixture was cooled to room temperature and the solid product was collected by filtration and chromatographed on silica gel using 95% chloroform/2.5% isopropyl alcohol/2.5% isopropylamine amine as eluant. The appropriate fractions were combined and evaporated to give 2.0 g 3-amino-6-methoxy-N,N-dimethyl-1H-pyrazolo[3,4-b]quinolin-1-acetamide, orange solid, m.p. 251°-253° C.

Workup

  1. temperatureat reflux for two hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe solid product was collected by filtration
  4. customchromatographed on silica gel using 95% chloroform/2.5% isopropyl alcohol/2.5% isopropylamine amine as eluant
  5. customevaporated

Sources & evidence

ORD record
ord-a049fb483a17429d9fdf7f5cce6f98d4
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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