4-Fluorobenzenesulfonyl isocyanate → N-{[(3-{[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)amino]carbonyl}-4-fluorobenzenesulfonamide

HRID 540832Notes

Reaction equation

HRID 540832 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:18]([CH2:24][CH2:25][CH3:26])=[N:17][C:11]=3[C:12]([NH2:16])=[N:13][C:14]=2[CH:15]=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([N:37]=[C:38]=[O:39])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[NH2:16][C:12]1[C:11]2[N:17]=[C:18]([CH2:24][CH2:25][CH3:26])[N:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:38]([NH:37][S:34]([C:31]3[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=3)(=[O:35])=[O:36])=[O:39])=[CH:15][C:14]=2[N:13]=1

Participants

4

Reactant 2

HCID 27333744-Fluorobenzenesulfonyl isocyanateHCID 588337127-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 58833666N-{[(3-{[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)amino]carbonyl}-4-fluorobenzenesulfonamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.500 g, 1.41 mmol) in chloroform (15 mL) was cooled to 0° C.; 4-fluorobenzenesulfonyl isocyanate (0.548 g, 2.72 mmol) was added in three portions over a period of 30 minutes. A white precipitate was present and was isolated by filtration, washed with chloroform, and dried overnight in a vacuum oven at 60° C. to provide 0.671 g of N-{[(3-{[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)amino]carbonyl}-4-fluorobenzenesulfonamide as a white powder, mp 194-198° C.

Workup

  1. customwas isolated by filtration
  2. washwashed with chloroform
  3. customdried overnight in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-bb2dc98ee3ae469f8539b62b0dec509a
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

Loading…