Реакция #40403

Уравнение реакции

N-methylethylenediamine

N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide

hydrogen sulfide

iodomethane

→

N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide

Растворители

methanol

acetic acid

triethyl amine

pyridine

Условия реакции

Обработка

1. 1
   ДругоеAfter the evaporated the solvent
2. 2
   workup.DISSOLUTIONthe residue was dissolved in anhydrous acetone (5 ml)
3. 3
   workup.STIRRINGThe mixture was stirred
4. 4
   Температураunder reflux condition for 2 hrs
5. 5
   ДругоеAfter the evaporation of solvent
6. 6
   workup.DISSOLUTIONthe residue was dissolved in anhydrous methanol (5 ml)
7. 7
   workup.STIRRINGThe mixture was stirred
8. 8
   Температураunder reflux condition for 2 hrs
9. 9
   ДругоеAfter the evaporation of solvent
10. 10
    Другоеthe crude residue was purified by RP-HPLC

Методика

To a solution of the compound of N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (683 mg, 1.66 mmol) in anhydrous pyridine (10 ml) and triethyl amine (1 ml) was saturated with hydrogen sulfide gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solvent, the residue was dissolved in anhydrous acetone (5 ml) and iodomethane (1 ml, 16.6 mmol) was added. The mixture was stirred under reflux condition for 2 hrs. After the evaporation of solvent, the residue was dissolved in anhydrous methanol (5 ml) and added a solution of N-methylethylenediamine (0.732 ml, 8.3 mmol) and acetic acid (1.5 ml) in anhydrous methanol (5 ml). The mixture was stirred under reflux condition for 2 hrs. After the evaporation of solvent, the crude residue was purified by RP-HPLC to give N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(1-methyl(2-imidazolin-2-yl))phenyl]carboxamide as a white powder. MS found for C23H19Cl2N5O2 M+=468 (M+2)+=470.

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