3-Chloropropanesulphonyl chloride → HCID 10093308, compound

HRID 2180305Notes

Reaction equation

HRID 2180305 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][CH2:21][CH2:22][CH3:23].Cl[CH2:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>CN1CCCC1=O>[CH2:20]([C:7]1[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:1]2[CH2:25][CH2:26][CH2:27][S:28]2(=[O:30])=[O:29])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=1)[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 155382261-(4-Aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10093308HCID 10093308, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Using the general method of Example 266 except that 1-methyl-2-pyrrolidinone was used in place of dichloromethane, 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (5.0 g, 16.0 mmol) was reacted with 3-chloropropanesulfonyl choride (2.83 g, 16.0 mmol) to provide 0.75 g of 2-butyl-1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 173.0-176.0° C.

Sources & evidence

ORD record
ord-cf808d24976a476d869765cc971f84d7
Source dataset
uspto-grants-2005_05
Patent number
US06888000B2

Reaction notes

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