4-Toluenesulfonyl chloride → HCID 57515390, compound

HRID 44704Notes

Reaction equation

HRID 44704 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2([O:24][CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:38].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>ClCCl.O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2([O:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:38])[C:8]=2[N:17]=1)[CH3:2]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57515391HCID 57515391, compound

Product 1

HCID 57515390HCID 57515390, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(ethoxymethyl)-1-[(1-methoxycyclopentyl)methyl]-1H-imidazo[4,5-c]quinoline (0.30 g, 0.88 mmol) in dichloromethane at rt was added m-CPBA (278 mg, 0.88 mmol). The solution was stirred for 1.5 h and concentrated ammonium hydroxide (5.73 mL) was added and the mixture was cooled in an ice bath. To the mixture was added TsCl (176 mg, 0.924 mmol). The mixture was stirred 3 h at rt. Water (10 mL) was added and the mixture was extracted with dichloromethane (3×20 mL). The combined organics were washed twice with brine, dried over Na2SO4, filtered, and concentrated to a yellow oil. The crude product was purified by flash chromatography (silica gel, gradient elution with 1-10% CMA/CHCl3). The purified product was crystallized from acetonitrile to provide 2-(ethoxymethyl)-1-[(1-methoxycyclopentyl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine as off white crystals (0.122 g, 39%) after vacuum drying at 80° C., mp 148.0-150.0° C.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringThe mixture was stirred 3 h at rt
  3. extractionthe mixture was extracted with dichloromethane (3×20 mL)
  4. washThe combined organics were washed twice with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow oil
  8. customThe crude product was purified by flash chromatography (silica gel, gradient elution with 1-10% CMA/CHCl3)
  9. customThe purified product was crystallized from acetonitrile

Sources & evidence

ORD record
ord-e51d857edab34967a4b85975ca69f896
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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