Dimethylformamide → HCID 66959079, compound

HRID 1984486Notes

Reaction equation

HRID 1984486 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][C:4]1[NH:5][N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17].C(=O)([O-])[O-].[K+].[K+].[Cl:25][CH2:26][CH2:27][CH2:28]I.CN(C=O)C>O>[Cl:25][CH2:26][CH2:27][CH2:28][N:5]1[C:4]([CH2:3][CH:2]([CH3:18])[CH3:1])=[C:16]2[C:7]([C:8]([NH2:17])=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=32)=[N:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 813631-Chloro-3-iodopropaneHCID 577175171-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 66959079HCID 66959079, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1-(2-Methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (2.4 g, 9.99 mmol, prepared as described in Example 9), potassium carbonate (5.5 g, 39.9 mmol), 3-chloroiodopropane (1.2 mL, 11.0 mmol), and DMF (110 mL) were combined and heated at 40° C. overnight. The reaction mixture was diluted with water and then extracted with ethyl acetate. The combined extracts were washed with water and concentrated under reduced pressure. The residue was purified twice by chromatography on a HORIZON HPFC system (silica gel eluting with ethyl acetate) to provide 2-(3-chloropropyl)-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified twice by chromatography on a HORIZON HPFC system (silica gel eluting with ethyl acetate)

Sources & evidence

ORD record
ord-ff55e5832aba46b4a931fdc476e19607
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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