Ethanol → (2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-[4-(pyridin-4-ylmethoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

HRID 1785918노트

반응식

HRID 1785918 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].BrC[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1.C(O)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:37]4[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=4)=[CH:27][CH:28]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 6427994-(Bromomethyl)pyridineHCID 10343669N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

생성물 1

HCID 10324580(2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-[4-(pyridin-4-ylmethoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The phenol was dissolved in DMF (5 mL) at room temperature. Sodium hydride (60% in oil) was added and the mixture allowed to stir 30 min. 4-Bromomethyl-pyridine was added and the reaction was allowed to stir over night. Ethanol was added and the reaction was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (2/98 methanol/dichloromethane-5/95 methanol/dichloromethane gradient) to afford the product.

후처리

  1. stirringto stir over night
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. customThe crude residue was purified by silica gel chromatography (2/98 methanol/dichloromethane-5/95 methanol/dichloromethane gradient)
  9. customto afford the product

출처 및 근거

ORD 기록
ord-aed14fa894c74c0081111ee7611cf940
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504508B2

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