Benzenesulfonyl chloride → HCID 10002420, compound

HRID 583873Notes

Reaction equation

HRID 583873 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:26])[C:16]=2[N:15]=[C:14]1[CH2:27][CH3:28].[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[NH2:26][C:17]1[C:16]2[N:15]=[C:14]([CH2:27][CH3:28])[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][S:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:37])=[O:36])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine2×HCID 22344443HCID 22344443, compound

Product 1

HCID 10002420HCID 10002420, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (1.18 mL, 8.5 mmol) was added to a mixture of 1-(4-aminobutyl)-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 7.1 mmol) and chloroform (200 mL). The resulting solution was chilled in an acetone/ice bath for 10 minutes. Benzenesulfonyl chloride (0.90 mL, 8.5 mmol) was slowly added over a period of 5 minutes. After 45 minutes 0.2 equivalents of triethylamine was added. After 6 hours the reaction mixture was washed with brine (2×250 mL) and with water (1×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from N,N-dimethylformamide. The recrystallized material and the filtrate were both slurried with methanol. The resulting solids were isolated by filtration, combined, and then dried in an Abderhalden drying apparatus overnight to provide 0.80 g of N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide as a white solid, m.p. 180.6-182.0° C. Analysis: Calculated for C22H25N5O2S.0.25 H2O: % C, 61.73; % H, 6.00; % N, 16.36; Found: % C, 61.79; % H, 6.04; % N, 16.43.

Workup

  1. temperatureThe resulting solution was chilled in an acetone/ice bath for 10 minutes
  2. washAfter 6 hours the reaction mixture was washed with brine (2×250 mL) and with water (1×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from N,N-dimethylformamide
  6. customThe resulting solids were isolated by filtration
  7. customdried in an Abderhalden drying apparatus overnight

Sources & evidence

ORD record
ord-5058787821864a5b8564fcccb936bb58
Source dataset
uspto-grants-2005_08
Patent number
US06924293B2

Reaction notes

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