Hydrochloric Acid → HCID 57515405, compound

HRID 1469265Notes

Reaction equation

HRID 1469265 reaction equation
Cl.[Si]([O:9][C:10]1([CH2:16][CH2:17][CH2:18][N:19]2[C:31]3[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[N:24]=[CH:23][C:22]=3[N:21]=[C:20]2[CH2:32][O:33][CH2:34][CH3:35])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(C(C)(C)C)(C)C>CO>[CH2:34]([O:33][CH2:32][C:20]1[N:19]([CH2:18][CH2:17][CH2:16][C:10]2([OH:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:21]=1)[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57515404HCID 57515404, compound

Product 1

HCID 57515405HCID 57515405, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An aqueous solution of 3 M HCl (3.0 mL) was added to a solution of 1-[3-(1-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)propyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline (prepared as described in part G, 3.16 mmol) in methanol (10 mL). A solid formed and additional methanol (10 mL) was added. The reaction was stirred at rt for 3 d and the solvent was removed in vacuo. The residue was dissolved in dichloromethane (40 mL) and saturated aqueous sodium bicarbonate (30 mL) was added so that the pH=8. The aqueous layer was extracted with dichloromethane (20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to yield 1-{3-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}cyclohexanol (1.14 g, 98%) as a brown gum.

Workup

  1. customA solid formed
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (40 mL)
  4. additionsaturated aqueous sodium bicarbonate (30 mL) was added so that the pH=8
  5. extractionThe aqueous layer was extracted with dichloromethane (20 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-92adbe953a0c44a89167d7eebd7f0032
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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