Sodium hydride → HCID 14822480, compound

HRID 2073779Notes

Reaction equation

HRID 2073779 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]3[C:15]([NH2:16])=[N:14][NH:13][C:9]3=[N:10]2)=[CH:5][CH:4]=1.Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]3[C:15]([NH2:16])=[N:14][N:13]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:9]3=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178487377HCID 178487377, compound

Product 1

HCID 14822480HCID 14822480, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 17.1 g 7-methoxy-1H-pyrazolo[3,4-b]quinolin-3-amine (Example 3d), 15.25 g 4-(2-chloroethyl)morpholine hydrochloride, 7.2 g sodium hydride and 500 ml dimethylformamide was stirred at room temperature for about 16 hours. The solvent was then removed by evaporation, and the residue dissolved in 1N hydrochloric acid and extracted with ethyl acetate. The aqueous layer was made basic with carbonate to pH 8 and extracted with chloroform. The chloroform extracts were washed with water, dried over magnesium sulfate and passed through a silica gel pad. The pad was eluted with warm ethyl acetate, the product isolated and recrystallized from ethyl acetate to give 9.2 g 7-methoxy-1-[2-(4-morpholinyl)ethyl]-1H-pyrazolo[3,4-b]quinolin-3-amine, orange solid, m.p. 166°-168° C.

Workup

  1. customThe solvent was then removed by evaporation
  2. dissolutionthe residue dissolved in 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. extractionextracted with chloroform
  5. washThe chloroform extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. washThe pad was eluted with warm ethyl acetate
  8. customthe product isolated
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7cd319e2dd0c4749bc8ec3717d88390f
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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