Methanesulfonyl chloride → HCID 10456186, compound

HRID 1839067Notes

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].[CH3:28][S:29](Cl)(=[O:31])=[O:30]>>[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:29]([CH3:28])(=[O:31])=[O:30])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

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

Product 1

HCID 10456186HCID 10456186, compoundYield 48.2%

Procedure

Using the general method of Example 242, 1-(8-aminooctyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 3.26 mmol) was reacted with methanesulfonyl chloride (260 μL, 3.26 mmol) to provide 0.70 g of N-[8-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)octyl]methanesulfonamide as a tan powder, m.p. 121-124° C. Analysis: Calculated for C23H35N5O3S: %C, 61.99: %H, 7.92; %N, 15.72; Found: %C, 62.01; %H, 7.97; %N, 15.75.

Sources & evidence

ORD record: ord-f20cf9077fca4805b95bf2ab70e00a75
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677349B1

Reaction notes

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