Methanesulfonyl chloride → HCID 10362916, compound

HRID 2180297Notes

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]=[CH:11]1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>>[NH2:23][C:14]1[C:13]2[N:12]=[CH:11][N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:25]([CH3:24])(=[O:27])=[O:26])[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 223444381-(8-Aminooctyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10362916HCID 10362916, compoundYield 28.7%

Procedure

Using the general method of Example 242, 1-(8-aminooctyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.85 mmol) was reacted with methanesulfonyl chloride (310 μL, 3.85 mmol) to provide 0.43 g of N-{8-[4-amino-1H-imidazo[4,5-c]quinolin-1-yl]octyl}methanesulfonamide as an off white powder, m.p. 153-155° C. Analysis: Calculated for C19H27N5O2S: % C, 58.59; % H, 6.99; % N, 17.98; % S, 8.23; Found: % C, 58.40; % H, 6.99; % N, 17.71; % S, 8.14.

Sources & evidence

ORD record: ord-d18e7ed098484ac28c098aa87fcde80d
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06888000B2

Reaction notes

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