Benzenesulfonyl chloride → HCID 86612263, compound

HRID 1623198Notes

Reaction equation

HRID 1623198 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[C:12]([O:16][C:17]([O:19][N:20]([CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:43]2[C:42]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[N:36]=[CH:35][C:34]=2[N:33]=[C:32]1[CH2:44][CH2:45][CH3:46])[C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18])([CH3:15])([CH3:14])[CH3:13].[OH-].[NH4+:48].C1(S(Cl)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[NH2:48][C:35]1[C:34]2[N:33]=[C:32]([CH2:44][CH2:45][CH3:46])[N:31]([CH2:30][CH2:29][CH2:28][CH2:27][N:20]([O:19][C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:18])[C:21](=[O:26])[C:22]([CH3:24])([CH3:23])[CH3:25])[C:43]=2[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[N:36]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86612262HCID 86612262, compound

Product 1

HCID 86612263HCID 86612263, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (75% purity, 4.03 g, 17.5 mmol) was added to a solution of N-[(tert-butoxycarbonyl)oxy]-2,2-dimethyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]propanamide (5.00 g, 10.0 mmol) in chloroform (975 mL). The reaction mixture was stirred at room temperature for 1.5 hours. The mixture was cooled to 0° C. and concentrated ammonium hydroxide (20 mL) was added, followed by benzene sulfonyl chloride (2.49 mL, 19.5 mmol). The reaction mixture was stirred for 2 hours at room temperature, then was transferred to a separatory funnel. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to afford 3.35 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-[(tert-butoxycarbonyl)oxy]-2,2-dimethylpropanamide.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customwas transferred to a separatory funnel
  4. customThe layers were separated
  5. washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4ed6d2ffabc74d2d95ae1f6b76937784
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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