3-(3-Cyanophenyl)-1-phenyl-2-propen-1-one → 3-(2-Morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine

HRID 2247866노트

반응식

HRID 2247866 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28](=[O:33])[CH2:29][C:30]([CH3:32])=O)[CH2:21][CH2:20]1.C([O-])(=O)C.[NH4+:38]>C(C(C)=O)C(C)C>[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]([C:29]2[C:30]([CH3:32])=[N:38][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]=2[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[O:33])[CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 3284303-(3-Cyanophenyl)-1-phenyl-2-propen-1-oneHCID 517165Ammonium AcetateHCID 4076516N-(2-morpholin-4-ylethyl)-3-oxobutanamide

생성물 1

HCID 198159053-(2-Morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine수율 29.7%

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매

실험 절차

To a solution of 3-(3-cyanophenyl)-1-phenyl-2-propen-1-one (4.7 g) in methyl isobutyl ketone (50 ml) were added N-(2-morpholinoethyl)acetoacetamide (6.5 g) and ammonium acetate (2.3 g), and the mixture was stirred at 80° to 85° C. for 4 hours. After cooling, the reaction mixture was washed with water and dried over magnesium sulfate. To the filtrate containing 1,4-dihydro-3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine and 3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine was added manganese dioxide (20 g) and the resultant mixture was stirred at 80° to 85° C. for 1.5 hours. Manganese dioxide was filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in diluted hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 8.0 with 20% aqueous solution of potassium carbonate, and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was subjected to a column chromatography on silica gel and eluted with a mixture of ethyl acetate and tetrahydrofuran (8:2 V/V). The fractions containing the desired compound were combined and concentrated in vacuo. The residue was recrystallized from diethyl ether to give 3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine (2.55 g).

후처리

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. additionTo the filtrate containing 1,4-dihydro-3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine and 3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine
  5. additionwas added manganese dioxide (20 g)
  6. stirringthe resultant mixture was stirred at 80° to 85° C. for 1.5 hours
  7. filtrationManganese dioxide was filtered off
  8. concentrationthe filtrate was concentrated in vacuo
  9. dissolutionThe residue was dissolved in diluted hydrochloric acid
  10. washwashed with ethyl acetate
  11. extractionextracted with ethyl acetate
  12. washThe extract was washed with brine
  13. dry with materialdried over magnesium sulfate
  14. customThe solvent was evaporated in vacuo
  15. washeluted with a mixture of ethyl acetate and tetrahydrofuran (8:2 V/V)
  16. additionThe fractions containing the desired compound
  17. concentrationconcentrated in vacuo
  18. customThe residue was recrystallized from diethyl ether

출처 및 근거

ORD 기록
ord-995437518581404aa80346c4baaf76d9
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05037824

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