Phenyl isocyanate → N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy)ethyl)-N'-phenylurea

温度

0 °C

1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (919 mg, 2.76 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. The reaction mixture was then treated with phenyl isocyanate (300 μL, 2.76 mmol) and Et3N (0.77 mL, 5.51 mmol) and allowed to warm slowly to room temperature. After stirring overnight, the reaction mixture was then quenched by addition of saturated NaHCO3 solution (30 mL). The organic layer was separated and washed with H2O and brine, dried over Na2SO4 and concentrated under reduced pressure to give a yellow solid. The solid was triturated with Et2O (30 mL) and a few drops of MeOH. The solid was isolated by filtration and dried under vacuum to give 460 mg of N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N′-phenylurea as a white powder. m.p. 180-182° C.;

1. temperatureto warm slowly to room temperature
2. customthe reaction mixture was then quenched by addition of saturated NaHCO3 solution (30 mL)
3. customThe organic layer was separated
4. washwashed with H2O and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customto give a yellow solid
8. customThe solid was triturated with Et2O (30 mL) and a few drops of MeOH
9. customThe solid was isolated by filtration
10. customdried under vacuum

ORDレコード

ord-bda6ec3f779147f5a9c5f89423944025

出典データセット

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07612083B2