Sodium Carbonate → N-[4-(4-Amino-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide

HRID 2383159Notes

Reaction equation

HRID 2383159 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][C:14]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:13][C:12]=3[N:11]=[C:10]([NH2:27])[C:9]=2[N:8]=[C:7]1[CH2:28][CH3:29].[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[NH2:27][C:10]1[C:9]2[N:8]=[C:7]([CH2:28][CH3:29])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[C:18]=2[C:17]2[CH:16]=[CH:15][C:14]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 670509391-(4-aminobutyl)-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 57545304N-[4-(4-Amino-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(4-Aminobutyl)-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (7.0 g, 18 mmol) was mixed with chloroform (180 mL), and the suspension was cooled with an ice/water bath. Methanesulfonyl chloride (1.59 mL, 20.5 mmol) was added dropwise, and the reaction was stirred for 18 hours. Saturated aqueous sodium carbonate was added to the solution, and the layers were separated. The precipitate in the aqueous layer was isolated by filtration, washed with ethanol and diethyl ether, and recrystallized from a mixture of methanol and chloroform. During the recrystallization, the hot solution was filtered through a glass fiber filter. N-[4-(4-Amino-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide (2.96 g) was isolated as an off-white solid. The organic layer was concentrated under reduced pressure, and the residue was stirred with boiling methanol and isolated by filtration to afford 1.90 g of N-[4-(4-amino-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide as a white solid, mp 213.5-215° C.

Workup

  1. temperaturethe suspension was cooled with an ice/water bath
  2. customthe layers were separated
  3. customThe precipitate in the aqueous layer was isolated by filtration
  4. washwashed with ethanol and diethyl ether
  5. customrecrystallized from a mixture of methanol and chloroform
  6. customDuring the recrystallization
  7. filtrationthe hot solution was filtered through a glass fiber
  8. filtrationfilter

Sources & evidence

ORD record
ord-dcb4f495817d4534b290e1a4c3258068
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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