Trifluoromethanesulfonic acid → HCID 10199786, compound

HRID 433171Notes

Reaction equation

HRID 433171 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH2:23][CH2:24][CH2:25][S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)C1C=CC=CC=1.OS(C(F)(F)F)(=O)=O>ClCCl>[C:29]1([S:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:21]2[C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=[C:9]([NH2:8])[C:18]=3[N:19]=[CH:20]2)(=[O:28])=[O:27])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 22320525HCID 22320525, compound

Product 1

HCID 10199786HCID 10199786, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, N,N-dibenzyl-1-[4-(phenylsulfonyl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 1.78 mmol), triflic acid (2.68 g, 17.83 mmol), and anhydrous dichloromethane (14 mL) under a nitrogen atmosphere. The reaction was judged to be complete after stirring at ambient temperature for 24 hours. The solution was partitioned between chloroform and excess aqueous sodium hydroxide (20%). The layers were separated. The aqueous layer was extracted with chloroform (3×). The organic layers were combined and then concentrated under reduced pressure to afford a light brown solid. The material was purified by chromatography over silica gel (90/10 dichloromethane/methanol) to provide a fine white powder which was recrystallized from acetonitrile to give 1-[4-(phenylsulfonyl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.32 g, 0.84 mmol) as white needles, m.p. 175-177° C.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customThe solution was partitioned between chloroform and excess aqueous sodium hydroxide (20%)
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with chloroform (3×)
  5. concentrationconcentrated under reduced pressure
  6. customto afford a light brown solid
  7. customThe material was purified by chromatography over silica gel (90/10 dichloromethane/methanol)
  8. customto provide a fine white powder which
  9. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b371b187974d412cbb23b8a5b09bb500
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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