Reaction #41578

Reaction equation

aniline

pyridine-2-carboxaldehyde

4-(2-chlorophenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

→

compound

5-(2-chloro-phenoxy)-2-pyridin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

Solvents

methanol

methanol

Conditions

Workup

1. 1
   Otherobtained in (step 1)
2. 2
   Otherthe reaction liquid
3. 3
   OtherThe solvent was evaporated away under reduced pressure
4. 4
   Otherthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
5. 5
   workup.ADDITIONThe solvent of the resulting fraction was diluted with ethyl acetate
6. 6
   Washwashed with aqueous saturated sodium bicarbonate
7. 7
   Dryingdried with anhydrous sodium sulfate
8. 8
   OtherThe solvent was evaporated away under reduced pressure

Procedure

0.26 ml of 1 M methanol solution of aniline and pyridine-2-carboxaldehyde (1/1) was added to a methanol (1 ml) solution of 35 mg of 4-(2-chlorophenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in (step 1), and the reaction liquid was stirred overnight at 60° C. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, and then dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a pale yellow solid.

Source