Thionyl Chloride → N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

HRID 2090241Notes

Reaction equation

HRID 2090241 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])[N:14]([CH2:15][CH2:16][CH2:17]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)(Cl)=O>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])[N:14]([CH2:15][CH2:16][CH2:17][NH:12][CH2:11][CH2:10][N:14]([CH3:15])[CH3:13])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 684322443-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol

Product 1

HCID 68432302N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product from step (v) (0.96 g) and thionyl chloride (10 mL) in DCM (20 mL) was heated under reflux for 6 h then evaporated under reduced pressure. The residue was dissolved in acetonitrile (20 mL) then N,N-dimethylethylenediamine (10 mL) added and the mixture heated under reflux for 24 h. The solvent was removed under reduced pressure and the residue purified by RPHPLC, yield 0.512 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. customthen evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  5. additionN,N-dimethylethylenediamine (10 mL) added
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 24 h
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by RPHPLC, yield 0.512 g

Sources & evidence

ORD record
ord-a6b876a359624606a34ae2bc2d260994
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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