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Water → 5-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736213
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인쇄 미리보기

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HRID 1736213 반응식
[NH2:1][C:2]1[C:7]2[C:8](=[O:27])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]([F:26])[CH:13]=3)[O:11][C:6]=2[C:5]([F:28])=[CH:4][C:3]=1[F:29].[H-].[Na+].[CH3:32][O:33][CH2:34]Cl.O>CN(C)C=O>[NH2:1][C:2]1[C:7]2[C:8](=[O:27])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:32][O:33][CH3:34])=[C:14]([F:26])[CH:13]=3)[O:11][C:6]=2[C:5]([F:28])=[CH:4][C:3]=1[F:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 19434972HCID 19434972, 화합물

생성물 1

HCID 194347945-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one수율 92.3%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

2.41 g (5.94 mmol) of Compound 51 obtained in Example 51 was dissolved in 60 mL of dimethylformamide under argon atmosphere, 237 mg (5.94 mmol) of sodium hydride (60% oil dispersion) and 0.47 mL (6.24mmol) of chloromethyl methyl ether were added under ice-cooling and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled on ice, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:acetonitrile=30:l) to give 2.47 g of 5-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one (yield: 92%).

후처리

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:acetonitrile=30:l)

출처 및 근거

ORD 기록
ord-c0e8acb201bd4856b7cb9f8981df71ef
출처 데이터셋
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05539112

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