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4-(Chloromethyl)benzoyl chloride → 4-chloromethyl-N-[2,4-dichloro-3-(1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-phenyl]-benzamide

HRID 270697
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HRID 270697 반응식
[NH2:1][C:2]1[C:3]([Cl:21])=[C:4]([C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[CH:14][CH:13]=3)[C:5]([Cl:8])=[CH:6][CH:7]=1.[Cl:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>ClCCl.CCOC(C)=O>[Cl:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([C:9]3[C:10](=[O:20])[N:11]([CH3:19])[C:12]4[C:17]([CH:18]=3)=[CH:16][N:15]=[CH:14][CH:13]=4)[C:3]=2[Cl:21])=[O:29])=[CH:26][CH:25]=1
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참가 물질

5

반응물 2

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 598338933-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]naphthyridin-2-one

생성물 1

HCID 598339014-chloromethyl-N-[2,4-dichloro-3-(1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-phenyl]-benzamide수율 73.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate
용매

실험 절차

To a solution of 3-(3-amino-2,6-dichloro-phenyl)-1-methyl-1H-[1,6]-naphthyridin-2-one (30 mg, 0.0937 mmol) in the dichloromethane (7 mL) is added 4-(chloromethyl)benzoyl chloride (53.2 mg, 0.28 mmol). After the mixture is stirred 24 hours at room temperature, it is diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column elute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (NH3, 2N)(95/5%) to give the titled intermediate as a solid (32.4 mg, 73.1%).

후처리

  1. washwashed with saturated K2CO3, brine and water
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customis purified by flash silica gel column
  7. washelute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (NH3, 2N)(95/5%)

출처 및 근거

ORD 기록
ord-1d13556be367482b9aa39fb91a016d1e
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449582B2

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