Hydrochloric Acid → HCID 67051107, compound

HRID 598372Notes

Reaction equation

HRID 598372 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][C:17]2[N:16]=[CH:15][C:14]3[N:20]=[C:21]([CH2:35][O:36][CH2:37][CH3:38])[N:22]([CH2:23][C:24]([NH:27]C(=O)OC(C)(C)C)([CH3:26])[CH3:25])[C:13]=3[C:12]=2[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][C:17]2[N:16]=[CH:15][C:14]3[N:20]=[C:21]([CH2:35][O:36][CH2:37][CH3:38])[N:22]([CH2:23][C:24]([NH2:27])([CH3:25])[CH3:26])[C:13]=3[C:12]=2[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86626177HCID 86626177, compound

Product 1

HCID 67051107HCID 67051107, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 50 mL solution of HCl in ethanol (4.3 M) was added to a solution of tert-butyl [2-(8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]carbamate (8.4 g, 16.6 mmol) in ethanol (50 mL) and heated at reflux temperature for 1 hour. The reaction was cooled to ambient temperature and nitrogen was bubbled through the solution. The solvent was removed under reduced pressure and water was added to the residue. The solution was made basic and then extracted with three portions of dichloromethane. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated to yield 6.26 g of 2-(8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethylamine as a brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1 hour
  3. customnitrogen was bubbled through the solution
  4. customThe solvent was removed under reduced pressure and water
  5. additionwas added to the residue
  6. extractionextracted with three portions of dichloromethane
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d2c3bf63a0794e329035d63880383b19
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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