Dichloromethane → N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide

HRID 583855Notes

Reaction equation

HRID 583855 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].C(N(CC)C(C)C)(C)C.ClCCl.[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:47]2[C:46]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[N:40]=[C:39]([NH2:48])[C:38]=2[N:37]=[C:36]1[CH2:49][CH2:50][CH2:51][CH3:52]>CO>[NH2:48][C:39]1[C:38]2[N:37]=[C:36]([CH2:49][CH2:50][CH2:51][CH3:52])[N:35]([CH2:34][CH2:33][CH2:32][CH2:31][NH:30][S:13]([C:8]3[C:9]4[C:4](=[C:3]([N:2]([CH3:17])[CH3:1])[CH:12]=[CH:11][CH:10]=4)[CH:5]=[CH:6][CH:7]=3)(=[O:15])=[O:14])[C:47]=2[C:46]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[N:40]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11801Dansyl chlorideHCID 81531DiisopropylethylamineHCID 155382261-(4-Aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 15538227N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamideYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Dimethylamino-1-naphthalenesulfonyl chloride (1.82 g, 6.74 mmol) was added to a mixture of N,N-diisopropylethylamine (1.23 mL, 7.06 mmol), dichloromethane (15 mL) and 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 6.42 mmol). The reaction mixture was allowed to stir at ambient temperature overnight. Methanol was added to the reaction mixture until a clear solution was obtained. Silica gel was added to the reaction mixture and then the solvents were removed. The silica gel was placed in a column and then eluted with chloroform in a stepwise gradient to 9:1 chloroform:methanol. The resulting product was recrystallized from N,N-dimethylformamide and deionized water to provide 2.5 g of N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide as a yellow crystalline solid, m.p. 223-224° C. Analysis: Calculated for C30H36N6O2S: % C, 66.15; % H, 6.66; % N, 15.43; Found: % C, 66.36; % H, 6.34; % N, 15.23.

Workup

  1. customwas obtained
  2. additionSilica gel was added to the reaction mixture
  3. customthe solvents were removed
  4. washeluted with chloroform in a stepwise gradient to 9:1 chloroform
  5. customThe resulting product was recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-48d2bdb8e31e422685edfe735d521d7f
Source dataset
uspto-grants-2005_08
Patent number
US06924293B2

Reaction notes

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