Benzenesulfonyl chloride → HCID 10029249, compound

HRID 1839071Notes

Reaction equation

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

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 223444481-(8-Aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10029249HCID 10029249, compoundYield 99.9%

Procedure

Using the general method of Example 242, 1-(8-aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 2.72 mmol) was reacted with benzenesulfonyl chloride (350 μL, 2.72 mmol) to provide 1.38 g of N-[8-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)octyl]benzenesulfonamide as an off white powder, m.p. 143-144° C. Analsysis: Calculated for C28H37N5O2S: %C, 66.24; %H, 7.35; %N, 13.79; Found: %C, 66.08; %H, 7.25; %N, 13.72. Karl Fisher titration found 0.23% water.

Sources & evidence

ORD record: ord-7ba7beccddc642c9a9124749d435ce48
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677349B1

Reaction notes

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