9-Aminoacridine → HCID 54507950, compound

HRID 479987Notes

Reaction equation

HRID 479987 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 540 in 350 mL of CHCl3 was added 2.9 mL (20.8 mmol) of Et3N and 4.50 g (20.6 mmol) 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 541 as an orange solid: 1H NMR (300 MHz, CDCl3, TMS) δ 9.25 (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-5de8a7ca0ffc431b874511ce714d6505
Source dataset
uspto-grants-2003_11
Patent number
US06649587B1

Reaction notes

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