Methane → tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

HRID 431456Notes

Reaction equation

HRID 431456 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[CH3:33][O:34][CH2:35][CH2:36][C:37](Cl)=O.C>C(Cl)Cl.CCO.CO>[CH3:33][O:34][CH2:35][CH2:36][C:37]1[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 8471Triethylamine2×HCID 27597283-Methoxypropanoyl chlorideHCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamate

Product 1

HCID 12106201tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamateYield 90.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (10.2 g, 29.5 mmol) in 250 mL of anhydrous CH2Cl2 was cooled to 0° C. and treated with triethylamine (4.18 mL, 30.0 mmol). Methoxypropionyl chloride (3.30 mL, 30.3 mmol) was then added dropwise over 5 min. The reaction was then warmed to room temperature and stirring was continued for 1 h. The reaction mixture was then concentrated under reduced pressure to give an orange solid. This was dissolved in 250 mL of EtOH and 12.5 mL of triethylamine was added. The mixture was heated to reflux and stirred under N2 overnight. The reaction was then concentrated to dryness under reduced pressure and treated with 300 mL of Et2O. The mixture was then filtered and the filtrate was concentrated under reduced pressure to give a brown solid. The solid was dissolved in 200 mL of hot MeOH and treated with activated charcoal. The hot solution was filtered and concentrated to give 11.1 g of tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate as a yellow syrup.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give an orange solid
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. stirringstirred under N2 overnight
  6. concentrationThe reaction was then concentrated to dryness under reduced pressure
  7. additiontreated with 300 mL of Et2O
  8. filtrationThe mixture was then filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto give a brown solid
  11. filtrationThe hot solution was filtered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-4aa5c045ed864718a0cd4ba8d051647b
Source dataset
uspto-grants-2003_12
Patent number
US06660735B2

Reaction notes

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