Methanesulfonyl chloride → HCID 10338633, compound

HRID 1839081Notes

Reaction equation

HRID 1839081 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:22])[C:12]=2[N:11]=[C:10]1[CH2:23][CH2:24][CH2:25][CH3:26]>N1C=CC=CC=1>[NH2:22][C:13]1[C:12]2[N:11]=[C:10]([CH2:23][CH2:24][CH2:25][CH3:26])[N:9]([CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[C:21]=2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22180889HCID 22180889, compound

Product 1

HCID 10338633HCID 10338633, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (1.27 g, 11.1 mmol) was slowly added to a solution of 1-(2-aminoethyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 10.6 mmol) in pyridine (60 mL). The reaction was maintained at ambient temperature overnight and then it was concentrated to dryness. The residue was combined with warm dichloroethane and water and then filtered to provide an off white solid. The dichloroethane layer was concentrated to provide an off white solid. The two solids were combined and then recrystallized from N,N-dimethylformamide to provide 1.1 g of N-[2-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide as a white solid, m.p. 210.0-211.0° C. Analysis: Calculated for C17H23N5O2S: %C, 56.49; %H, 6.41; %N, 19.37; Found: %C, 56.45; %H, 6.49; %N, 19.50.

Workup

  1. concentrationit was concentrated to dryness
  2. filtrationfiltered
  3. customto provide an off white solid
  4. concentrationThe dichloroethane layer was concentrated
  5. customto provide an off white solid
  6. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-5c790fb80cd7499e8a9acbe7cf8dcb34
Source dataset
uspto-grants-2004_01
Patent number
US06677349B1

Reaction notes

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