4-Toluenesulfonyl chloride → N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-4-methylbenzenesulfonamide

HRID 2180291Notes

Reaction equation

HRID 2180291 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][CH2:21][CH3:22].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][CH2:21][CH3:22])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][S:29]([C:26]3[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=3)(=[O:31])=[O:30])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 223444131-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10095356N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-4-methylbenzenesulfonamideYield 69%

Procedure

Using the general method of Example 245 1-(3-aminopropyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 5.04 mmol) was reacted with p-toluenesulfonyl chloride (1.08 g, 5.55 mmol) to provide 1.57 g of N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-4-methylbenzenesulfonamide as an off white powder, m.p. 197.0-198.5° C. Analysis: Calculated for C24H29N5O2S: % C, 63.83; % H, 6.47; % N, 15.51; Found: % C, 63.68; % H, 6.40; % N, 15.51.

Sources & evidence

ORD record
ord-6a1ba582a0bd4e579dbacb98ec68b829
Source dataset
uspto-grants-2005_05
Patent number
US06888000B2

Reaction notes

Loading…