Benzenesulfonyl chloride → HCID 58967533, compound

HRID 909341Notes

Reaction equation

HRID 909341 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:24][CH2:25][CH2:26][O:27][CH:28]([CH3:30])[CH3:29])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([N:17]4[CH2:21][CH2:20][CH2:19][C:18]4=[O:22])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:23]=1)[CH3:2].ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:43].C1(S(Cl)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[NH2:43][C:9]1[C:8]2[N:23]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:24][CH2:25][CH2:26][O:27][CH:28]([CH3:29])[CH3:30])[C:7]=2[C:16]2[CH:15]=[CH:14][C:13]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67381991HCID 67381991, compound

Product 1

HCID 58967533HCID 58967533, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
2 °C

Procedure

1-[2-Ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyrrolidin-2-one (0.38 g) was dissolved in chloroform (10 mL). 3-Chloroperoxybenzoic acid (60% pure, 0.37 g) was added in one portion and the mixture was allowed to stir for 16 hours. Ammonium hydroxide (10 mL) was added and the biphasic mixture was cooled to 2° C. with an ice/water bath. Benzenesulfonyl chloride (0.22 mL) was added and the reaction was stirred for 3 hours. The layers were separated and the aqueous fraction was extracted with chloroform. The combined organic fractions were sequentially washed with water and saturated aqueous sodium chloride; dried over anhydrous sodium sulfate; filtered and concentrated under reduced pressure. The residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform:CMA in a gradient from 99:1 to 73:27. Fractions containing product were combined and concentrated under reduced pressure. The residue was recrystallized from acetonitrile to afford 0.14 g of 1-[4-amino-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyrrolidin-2-one as a white solid, mp 165-167° C.

Workup

  1. stirringthe reaction was stirred for 3 hours
  2. customThe layers were separated
  3. extractionthe aqueous fraction was extracted with chloroform
  4. washThe combined organic fractions were sequentially washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument
  9. customThe purification
  10. washwas carried out eluting with chloroform
  11. additionFractions containing product
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c3ae54ab8e254f5384194406b5653cf9
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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