Hydrochloric Acid → 2-ethoxymethyl-1-(piperidin-4-ylmethyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine trihydrochloride

HRID 9393Notes

Reaction equation

HRID 9393 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:30][O:31][CH2:32][CH3:33])[N:15]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:11]=2[C:10]2[CH:9]=[CH:8][C:7]([C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)=[CH:6][C:5]=2[N:4]=1>C(O)C>[ClH:1].[ClH:1].[ClH:1].[CH2:32]([O:31][CH2:30][C:14]1[N:15]([CH2:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[CH:6][C:5]=3[N:4]=[C:3]([NH2:2])[C:12]=2[N:13]=1)[CH3:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21984389tert-butyl 4-{[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidine-1-carboxylate

Product 1

HCID 219842792-ethoxymethyl-1-(piperidin-4-ylmethyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine trihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanolic hydrochloric acid (17.68 mL of 4.25 M) was added to a solution of tert-butyl 4-{[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidine-1-carboxylate (9.71 g, 18.8 mmol) in anhydrous ethanol, and the reaction was heated at reflux for two hours. A precipitate formed, and the reaction was allowed to cool to ambient temperature. The solid was isolated by filtration, washed with a small volume of cold ethanol, and dried under reduced pressure to provide 7.1 g of 2-ethoxymethyl-1-(piperidin-4-ylmethyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine trihydrochloride as an off-white solid, mp>250° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for two hours
  3. customA precipitate formed
  4. customThe solid was isolated by filtration
  5. washwashed with a small volume of cold ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7f6c6e3fc28f475d81766645384bb24d
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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