Sodium hydride → 2-(5-fluoro-4-formyl-2-methoxy-phenoxymethyl)-1H-benzoimidazole-5-sulfonic acid dimethylamide

HRID 253476

반응식

HRID 253476 반응식
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl.[CH3:16][N:17]([CH3:32])[S:18]([C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26]([CH2:28]Cl)=[N:27][C:23]=2[CH:22]=1)(=[O:20])=[O:19]>CN(C)C=O>[CH3:32][N:17]([CH3:16])[S:18]([C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26]([CH2:28][O:10][C:8]3[CH:9]=[C:2]([F:1])[C:3]([CH:4]=[O:5])=[CH:6][C:7]=3[O:11][CH3:12])=[N:27][C:23]=2[CH:22]=1)(=[O:19])=[O:20]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehydeHCID 1784861302-Chloromethyl-1h-benzoimidazole-5-sulfonic acid dimethylamide hydrochloride salt

생성물 1

HCID 1784926252-(5-fluoro-4-formyl-2-methoxy-phenoxymethyl)-1H-benzoimidazole-5-sulfonic acid dimethylamide수율 17%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

2-Fluoro-4-hydroxy-5-methoxy-benzaldehyde (39, 0.38 g, 2.2 mmol) was dissolved in N,N-dimethylformamide (30 mL) and sodium hydride 60% dispersion in mineral oil (120 mg) was added. After 20 minutes, 2-chloromethyl-1H-benzoimidazole-5-sulfonic acid dimethylamide hydrochloride salt (217, 0.559 g, 1.80 mmol) was added to the mixture. The reaction was stirred at 60° C. overnight. The solvent was removed under reduced pressure. Ethyl acetate was added and the organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with a gradient of ethyl acetate (20-100%) in hexane to provide the desired compound (218, 0.122 g, 17%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionEthyl acetate was added
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with a gradient of ethyl acetate (20-100%) in hexane

출처 및 근거

ORD 기록
ord-6e5000b5af3948089cfc1951e1941618
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872018B2

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