9-Aminoacridine → HCID 54507950, compound

HRID 1018752Notes

Reaction equation

HRID 1018752 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CCN(CC)CC.[C:23]1([CH3:35])[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:24]=1[S:31](Cl)(=[O:33])=[O:32]>C(Cl)(Cl)Cl>[CH:4]1[C:3]2[C:8](=[N:9][C:10]3[C:15]([C:2]=2[NH:1][S:31]([C:24]2[C:25]([CH3:30])=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=2[CH3:35])(=[O:33])=[O:32])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 70199-AminoacridineHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chloride

Product 1

HCID 54507950HCID 54507950, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 4.00 g (20.6 mmol) of 9-aminoacridine 40 in 350 mL of CHCl3 was added 2.9 mL (20.8 mmol) of Et3N and 4.50 g (20.6 mmmol) of mesitylenesulfonyl chloride. The reaction mixture was refluxed for 72 hr. Then the reaction mixture was filtered and the solvent was evaporated. The material was purified by column chromatography on silica gel by eluting first with 1% MeOH in CH2Cl2 and then with 5% MeOH in CH2Cl2 to yield 458.4 mg (6%) of sulfonamide 41 as an orange solid: 1H NMR (300 MHz, CDCl3, TMS) δ9.25 (s, 1H), 8.77 (d, J=8 Hz, 2H), 7.46 (t, J=8 Hz, 2H), 7.21 (d, J=8 Hz, 2H), 7.15 (t, J=8 Hz, 2H), 7.02 (s, 2H), 2.78 (s, 6H), 2.36 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 72 hr
  2. filtrationThen the reaction mixture was filtered
  3. customthe solvent was evaporated
  4. customThe material was purified by column chromatography on silica gel
  5. washby eluting first with 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-3766980147464b79bd277d8fdf19ef91
Source dataset
uspto-grants-2002_11
Patent number
US06482943B1

Reaction notes

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