HCID 14822491, compound → HCID 14822492, compound

HRID 2073782Notes

Reaction equation

HRID 2073782 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:20]2[C:11](=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=3)[N:10]([CH2:23][C:24]([NH:26][CH3:27])=O)[N:9]=1>O1CCCC1>[CH3:27][NH:26][CH2:24][CH2:23][N:10]1[C:11]2=[N:12][C:13]3[C:18]([CH:19]=[C:20]2[C:8]([NH2:7])=[N:9]1)=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=3

Participants

4

Reactant 2

HCID 14822491HCID 14822491, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14822492HCID 14822492, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.00 lithium aluminum hydride in 100 ml tetrahydrofuran was added, portionwise, 5.5 g 3-amino-6-methoxy-N-methyl-1H-pyrazolo[3,4-b]quinolin-1-acetamide (Example 26) and 50 ml of tetrahydrofuran. The mixture was heated at reflux for 4 hours, then cooled and poured into ice-water. The solid product was collected and chromatographed on silica gel using 95% chloroform/5% isopropylamine as eluant. The fractions were combined and evaporated, and the product recrystallized from ether/hexane to give 0.77 g 1-[2-(methylamino)ethyl]-6-methoxy-1H-pyrazolo[3,4-b]quinolin-3-amine, orange solid, m.p. 142°-144° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 4 hours
  4. temperaturecooled
  5. customThe solid product was collected
  6. customchromatographed on silica gel using 95% chloroform/5% isopropylamine as eluant
  7. customevaporated
  8. customthe product recrystallized from ether/hexane

Sources & evidence

ORD record
ord-0bb41dd2724243dd9a73c74f66ed4c24
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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