Isopropyl isocyanate → N-{4-[4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N'-(1-methylethyl)urea

HRID 9510Notes

Reaction equation

HRID 9510 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]([Br:19])=[CH:13][C:12]=3[N:11]=[C:10]([NH2:20])[C:9]=2[N:8]=[C:7]1[CH2:21][O:22][CH2:23][CH3:24].[CH:25]([N:28]=[C:29]=[O:30])([CH3:27])[CH3:26]>C(Cl)(Cl)Cl>[NH2:20][C:10]1[C:9]2[N:8]=[C:7]([CH2:21][O:22][CH2:23][CH3:24])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:29]([NH:28][CH:25]([CH3:27])[CH3:26])=[O:30])[C:18]=2[C:17]2[CH:16]=[CH:15][C:14]([Br:19])=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 219841661-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 21984035N-{4-[4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N'-(1-methylethyl)ureaYield 76.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.1 mmol) in chloroform (36 mL) was cooled to 0° C., and a cold solution of isopropyl isocyanate (0.50 mL, 5.4 mmol) in chloroform (4 mL) was added slowly. A precipitate formed, and the reaction was stirred for 45 minutes. The reaction mixture was triturated with ethyl acetate (200 mL), and the precipitate was isolated by filtration and dried for three days in a drying oven to provide 1.86 g of N-{4-[4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}—N′-(1-methylethyl)urea as a white solid, mp 211° C.

Workup

  1. customA precipitate formed
  2. customThe reaction mixture was triturated with ethyl acetate (200 mL)
  3. customthe precipitate was isolated by filtration
  4. customdried for three days in a drying oven

Sources & evidence

ORD record
ord-0094d8a37a7a4e47843d835197d1b45e
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

Loading…