HCID 22096925, Verbindung → 857002-72-3

In a reactor, 300 mg (1.1 mmol) of 2-methyl-4-[N,N-bis(2-chloroethyl)amino]nitrobenzene were dissolved in a mixed solvent of 5 ml of methanol and 2 ml of tetrahydrofuran, followed by the addition of 200 mg of 10% Pd/C under a nitrogen gas atmosphere. The reactor was purged with hydrogen gas, followed by stirring at room temperature for one hour. After completion of the reaction, the reactor was purged with nitrogen gas, followed by stirring for 30 minutes. The 10% Pd/C was then filtered off. To the thus-obtained methanol solution, 400 μl of a solution of 4N hydrochloric acid/dioxane were added, whereby 2-methyl-4-[N,N-bis(2-chloroethyl)amino]aniline hydrochloride was obtained. In 10 ml of DMF, 309 mg (1.1 mmol) of 1H-2-(1-methyl-4-nitropyrrol-2-yl)benzimidazole-5-carboxylic acid and the 2-methyl-4-[N,N-bis(2-chloroethyl)amino]aniline hydrochloride obtained above were dissolved, followed by cooling to 0° C. Under a nitrogen gas atmosphere, 330 μl (2.4 mmol) of triethylamine and then 197 μl (1.3 mmol) of DECP were added to the resultant solution, followed by stirring for 20 minutes as was. Stirring was conducted for further 15 minutes at room temperature. The reaction mixture was then allowed to stand overnight. The solvent was distilled out under reduced pressure. The residue so obtained was purified by chromatography on a silica gel column (ethyl acetate/n-hexane=1/1), whereby 329 mg of yellow powder were obtained (yield: 59%).

1. customThe reactor was purged with hydrogen gas
2. customAfter completion of the reaction
3. customthe reactor was purged with nitrogen gas
4. stirringby stirring for 30 minutes
5. filtrationThe 10% Pd/C was then filtered off
6. additionTo the thus-obtained methanol solution, 400 μl of a solution of 4N hydrochloric acid/dioxane were added

ORD-Eintrag

ord-5e92b2490e23454a8ac6df21149a11f1

Quelldatensatz

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05852011