Dansyl chloride → HCID 10346982, compound

HRID 583897Notes

Reaction equation

HRID 583897 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][O:21][CH3:22].[CH3:23][N:24]([CH3:39])[C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][CH:29]=[C:30]2[S:35](Cl)(=[O:37])=[O:36]>C(Cl)(Cl)Cl>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][O:21][CH3:22])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][S:35]([C:30]3[C:31]4[C:26](=[C:25]([N:24]([CH3:39])[CH3:23])[CH:34]=[CH:33][CH:32]=4)[CH:27]=[CH:28][CH:29]=3)(=[O:37])=[O:36])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 11801Dansyl chlorideHCID 223444281-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10346982HCID 10346982, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the general method of Example 245 except that chloroform was used as the solvent, 1-(3-aminopropyl)-2-(methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.53 g, 5.11 mmol) was reacted with 5-dimethylamino-1-naphthalenesulfonyl chloride (5.87 mmol) to provide 1.45 g of N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}-5-(dimethylamino)naphthalene-1-sulfonamide as a yellow solid, m.p. 210-215° C. Analysis: Calculated for C28H32N6O3S.1.50 H2: % C, 60.09; % H, 6.30; % N; 15.02; Found: % C, 59.89; % H, 6.22; % N, 14.86.

Sources & evidence

ORD record
ord-8a85c1b3fb2b4f7796dd1ec0043a0d07
Source dataset
uspto-grants-2005_08
Patent number
US06924293B2

Reaction notes

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