Dimethylformamide → HCID 66959079, compound

HRID 2283886Notes

Reaction equation

HRID 2283886 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-8846baeff42f4f2187fe601236b92b0b
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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