4-Toluenesulfonyl chloride → HCID 67052438, compound

HRID 1907971Notes

Reaction equation

HRID 1907971 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:13]([CH2:19][Cl:20])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:33].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:13]([CH2:19][Cl:20])=[N:12][C:7]=3[C:8]([NH2:33])=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67052459HCID 67052459, compound

Product 1

HCID 67052438HCID 67052438, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 7-bromo-2-(chloromethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (13.9 g, 39.4 mmol) in chloroform (300 mL) at room temperature was added mCPBA (77% pure, 17.7 g, 78.8 mmol) over ten minutes. The reaction mixture was stirred at room temperature for 3 hours, then concentrated ammonium hydroxide (150 mL) was added, followed by p-toluenesulfonyl chloride (9.00 g, 47.3 mmol, added in portions over 10 minutes). The mixture was stirred at room temperature for 1 hour, then was transferred to a separatory funnel. The layers were separated and the aqueous layer was extracted with dichloromethane (2×100 mL). The organic layers were combined, dried over magnesium sulfate, filtered through CELITE filter agent, and concentrated under reduced pressure. The crude product was purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with ethyl acetate in hexanes) to yield 7.69 g of 7-bromo-2-(chloromethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a yellow foam.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. customwas transferred to a separatory funnel
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through CELITE
  7. filtrationfilter agent
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by chromatography
  10. washa HORIZON HPFC system (silica gel, gradient elution with ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-37785250188c42ac8c617422e44a8719
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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