Methane → HCID 10359216, compound

HRID 431489Notes

Reaction equation

HRID 431489 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:28][O:29][CH2:30][CH3:31])[N:14]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.CCOCC.C>Cl.CCO.CO>[NH2:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:28][O:29][CH2:30][CH3:31]

Participants

7

Reactant 3

HCID 297MethaneHCID 3283Diethyl EtherHCID 21936590HCID 21936590, compound

Product 1

HCID 10359216HCID 10359216, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Tert-butyl 2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate (14.45 g, 33.6 mmol) was dissolved in 50 mL of 2M HCl in EtOH and the mixture was heated to reflux with stirring. After 3 h, the reaction was cooled to room temperature and treated with ether (100 mL). The HCl salt of the product was collected by vacuum filtration The free base was made by dissolving the hydrochloride salt in 75 mL of water and treating with concentrated NH4OH until pH 12 was reached. The aqueous suspension was extracted with CH2Cl2 (4×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to give a thick orange oil. The oil was dissolved in MeOH (100 mL), treated with 2 g of activated charcoal and heated to reflux. After 2 h, the mixture was filtered through a pad of Celite and rinsed with portions of MeOH. The filtrate was concentrated to yield 1-[2-(2-aminoethoxy)ethyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a sticky orange solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationThe HCl salt of the product was collected by vacuum filtration The free base
  4. dissolutionby dissolving the hydrochloride salt in 75 mL of water
  5. additiontreating with concentrated NH4OH until pH 12
  6. extractionThe aqueous suspension was extracted with CH2Cl2 (4×50 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customto give a thick orange oil
  10. temperatureheated to reflux
  11. waitAfter 2 h
  12. filtrationthe mixture was filtered through a pad of Celite
  13. washrinsed with portions of MeOH
  14. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2571696e42754a36b0909df2ef18bfef
Source dataset
uspto-grants-2003_12
Patent number
US06660735B2

Reaction notes

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