Methanesulfonyl chloride → HCID 10338633, compound

HRID 583901Notes

Reaction equation

HRID 583901 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-22c5639ab4a54a88b88031fdd818e71e
Source dataset
uspto-grants-2005_08
Patent number
US06924293B2

Reaction notes

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