Hydrochloric Acid → HCID 57515405, compound

HRID 44727Notes

Reaction equation

HRID 44727 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-8fe7484c643a42129e184968ee500f18
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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