4-Toluenesulfonyl chloride → HCID 67052320, compound

HRID 1907953Notes

Reaction equation

HRID 1907953 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][C:28]([CH3:31])([OH:30])[CH3:29])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1.[OH-].[NH4+:33].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:33][C:18]1[C:17]2[N:26]=[C:14]([CH2:13][Cl:12])[N:15]([CH2:27][C:28]([CH3:31])([OH:30])[CH3:29])[C:16]=2[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67052488HCID 67052488, compound

Product 1

HCID 67052320HCID 67052320, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (77% pure, 36.5 g, 163 mmol) was added over 10 minutes to a stirred suspension of 1-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (23.6 g, 81.4 mmol) in chloroform (500 mL). The resulting solution was stirred at room temperature for 1.5 hours. Concentrated ammonium hydroxide (200 mL) was added. After 5 minutes, p-toluenesulfonyl chloride (18.6 g, 97.7 mmol) was added in portions. The mixture was stirred at room temperature for 2.3 hours, then was transferred to a separatory funnel. The layers were separated and the aqueous layer was extracted with dichloromethane (2×100 mL, then 3×200 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a foam. The crude product was purified in portions by chromatography on a HORIZON HPFC system (silica gel, elution with 5% methanol in chloroform followed by gradient elution with 5-15% methanol in chloroform) to yield 9.42 g of 1-[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as a pale yellow solid.

Workup

  1. waitAfter 5 minutes
  2. stirringThe mixture was stirred at room temperature for 2.3 hours
  3. customwas transferred to a separatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a foam
  10. customThe crude product was purified in portions by chromatography on a HORIZON HPFC system (silica gel, elution with 5% methanol in chloroform followed by gradient elution with 5-15% methanol in chloroform)

Sources & evidence

ORD record
ord-ee5f8860745342809490fa5cd49f91de
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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