HCID 57657258, compound → HCID 57657259, compound

HRID 244847Notes

Reaction equation

HRID 244847 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21]C)[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:5][C:4]=2[N:3]=1>ClCCl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][OH:21])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:5][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 57657258HCID 57657258, compound

Product 1

HCID 57657259HCID 57657259, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirring solution of 1-{4-amino-2-(methoxymethyl)-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (340 mg, 0.84 mmol) in dichloromethane (40 mL) was sealed with a septum and purged with nitrogen gas. The solution was cooled in an ice/water bath and a 1.0 M solution of boron tribromide in dichloromethane (4.2 mL) was added via syringe. The resulting mixture was stirred for 18 hours while warming to ambient temperature. The mixture was cooled back to 0° C. in an ice/water bath and the second portion of boron tribromide (1.0 M, 4.2 mL) was added. The reaction was stirred for 3 hours while warming to ambient temperature. Methanol (30 mL) was added and the mixture was concentrated to a purple foam. The foam was dissolved in 10% aqueous hydrochloric acid (30 ml) and washed with chloroform (2×25 mL). The aqueous fraction was neutralized by the slow addition of solid potassium carbonate until the pH reached 11. The aqueous fraction was extracted with chloroform (2×50 mL) and allowed to stand overnight. The resulting solid was recovered by filtration to provide 126 mg of 1-{4-amino-2-(hydroxymethyl)-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol

Workup

  1. custompurged with nitrogen gas
  2. temperatureThe solution was cooled in an ice/water bath
  3. additiona 1.0 M solution of boron tribromide in dichloromethane (4.2 mL) was added via syringe
  4. temperatureThe mixture was cooled back to 0° C. in an ice/water bath
  5. additionthe second portion of boron tribromide (1.0 M, 4.2 mL) was added
  6. stirringThe reaction was stirred for 3 hours
  7. temperaturewhile warming to ambient temperature
  8. additionMethanol (30 mL) was added
  9. concentrationthe mixture was concentrated to a purple foam
  10. dissolutionThe foam was dissolved in 10% aqueous hydrochloric acid (30 ml)
  11. washwashed with chloroform (2×25 mL)
  12. additionThe aqueous fraction was neutralized by the slow addition of solid potassium carbonate until the pH
  13. extractionThe aqueous fraction was extracted with chloroform (2×50 mL)
  14. waitto stand overnight
  15. filtrationThe resulting solid was recovered by filtration

Sources & evidence

ORD record
ord-cff8a6a286d640efa6b132045a92ce91
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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