Sodium hydride → 4-[(2,4-dichlorophenyl)amino]-3-{2-[4-(1-ethoxyethoxy)phenyl]-1-methyl-2-oxoethyl}-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one

HRID 2102873노트

반응식

HRID 2102873 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH2:15][CH2:14][N:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12](=[O:22])[CH:11]=1.[H-].[Na+].Br[CH:26]([CH3:41])[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([O:38][CH2:39][CH3:40])[CH3:37])=[CH:31][CH:30]=1)=[O:28]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH2:15][CH2:14][N:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12](=[O:22])[C:11]=1[CH:26]([CH3:41])[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([O:38][CH2:39][CH3:40])[CH3:37])=[CH:31][CH:30]=1)=[O:28]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 442497124-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-oneHCID 442497132-Bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-one

생성물 1

HCID 250296504-[(2,4-dichlorophenyl)amino]-3-{2-[4-(1-ethoxyethoxy)phenyl]-1-methyl-2-oxoethyl}-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one수율 138.9%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

4-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one (450 mg, 1.323 mmol) suspended in THF (7 ml) was added during 15 min to NaH (67 mg, 2.645 mmol) suspended in THF (5 ml) at 5° C. under nitrogen. After the resulting mixture had been stirred at 0° C. for 1 h tetrabutylammonium iodide (49 mg, 0.132 mmol) was added followed by dropwise addition of 2-bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-one (597 mg, 1.984 mmol) dissolved in THF (5 ml) during 15 min. After the addition the cooling bath was removed and the reaction was continued at rt overnight. Water was added and the solvent was removed by evaporation. The residue was partitioned between DCM and water. The organic phase was dried (MgSO4), filtered and evaporated to yield an orange oil (1.030 g, 90%).

후처리

  1. additionwas added
  2. additionAfter the addition the cooling bath
  3. customwas removed
  4. additionWater was added
  5. customthe solvent was removed by evaporation
  6. customThe residue was partitioned between DCM and water
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-f19bad9e5e5e414f8ac117ac4af3749f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576095B2

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