반응 #78434

반응 방정식

chloride

4-(3-chloro-phenyl)-6-[(5-chloro-pyridin-2-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-methyl-1H-quinolin-2-one

chloride

potassium carbonate

cyclopropylamine

→

title compound

수율 32.1%

4-(3-Chloro-Phenyl)-6-[(5-Chloro-Pyridin-2-yl)-Cyclopropylamino-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-1-Methyl-1H-Quinolin-2-One

수율 32.1%

용매

DMF

반응 조건

후처리

1. 1
   기타was partitioned between CHCl3 and water
2. 2
   세척The organic layer was washed with brine
3. 3
   건조dried over MgSO4
4. 4
   농축concentrated under vacuum
5. 5
   기타to give the crude product
6. 6
   기타It was chromatographed on silica gel with MeOH—CHCl3—NH4OH (2:98:0.2 to 5:95:0.5) as eluents

실험 절차

For the formation of the correspondent chloride, the same procedure was used as that in example 2, except that 4-(3-chloro-phenyl)-6-[(5-chloro-pyridin-2-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-methyl-1H-quinolin-2-one (55 mg, 0.112 mmol) was used in the place of 4-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1H-quinolin-2-one. The obtained chloride was dissolved in DMF (8 ml). To this solution were added potassium carbonate (K2CO3) and cyclopropylamine (0.049 ml, 0.786 mmol). The reaction mixture was stirred at ambient temperature for 15 hours after which time it was partitioned between CHCl3 and water. The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to give the crude product. It was chromatographed on silica gel with MeOH—CHCl3—NH4OH (2:98:0.2 to 5:95:0.5) as eluents to afford the title compound as a white solid (19 mg, 0.036 mmol, 32% yield).

출처