4-Toluenesulfonyl chloride → HCID 11395063, compound

HRID 2362499Notes

Reaction equation

HRID 2362499 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].[OH-].[NH4+:31].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[NH2:31][C:9]1[C:8]2[N:18]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:6]([CH2:19][CH2:20][CH2:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68933611HCID 68933611, compound

Product 1

HCID 11395063HCID 11395063, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a vigorously stirred mixture of the 4-(2-butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one from the previous step in dichloromethane (49 mL) and ammonium hydroxide (16 mL) was added p-toluenesulfonyl chloride (2.34 g, 12.3 mmol) portionwise over several minutes. After 15 minutes the reaction mixture was diluted with chloroform (200 mL) and saturated aqueous sodium bicarbonate solution (100 mL). The layers were separated and the organic phase was washed again with a saturated aqueous sodium bicarbonate solution (100 mL). The aqueous portions were then back extracted with chloroform (50 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated to a dark yellow solid. The dark yellow solid was slurried in diethyl ether and filtered to form a fine off-white solid. This solid was recrystallized from N,N-dimethylformamide (DMF) and water to afford 4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one as an off-white fluffy solid, mp 178-180° C.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed again with a saturated aqueous sodium bicarbonate solution (100 mL)
  3. extractionThe aqueous portions were then back extracted with chloroform (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a dark yellow solid
  7. filtrationfiltered
  8. customto form a fine off-white solid
  9. customThis solid was recrystallized from N,N-dimethylformamide (DMF) and water

Sources & evidence

ORD record
ord-a57242858ec5401dbc81f7013dfc963a
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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