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

HRID 1818256Notes

Reaction equation

HRID 1818256 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-f8b0e575531b4c0089b90e4272c05c03
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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