Water → 7-chloro-3-(2-methylsulfonylaminobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione

HRID 2301293노트

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HRID 2301293 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:23])(=[O:10])=[O:9].[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>N1C=CC=CC=1>[Cl:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[N:11]([S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][S:25]([CH3:24])(=[O:27])=[O:26])(=[O:10])=[O:9])[C:12](=[O:23])[NH:13]2)=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 98413923-(2-Aminobenzenesulfonyl)-7-Chloro-2,4(1H,3H)-Quinazolinedione

생성물 1

HCID 98673267-chloro-3-(2-methylsulfonylaminobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione수율 66.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

22 mg (0.06 mmol) of Compound 2 was dissolved in 200 μl of pyridine, 11.6 μl (0.15 mmol) of methanesulfonyl chloride was added dropwise, then the resultant mixture was stirred at room temperature overnight. An excess amount of water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous hydrochloric acid solution and saturated saline, then dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The crude product was crystallized from diethyl ether to obtain 16 mg (0.04 mmol) of the above-identified compound. Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δ ppm, DMSO-d6): 3.61 (3H, s), 7.10 (1H, d), 7.20 (1H, d), 7.74 (1H, d), 7.82-7.90 (4H, m), 8.34 (1H, d), 11.70 (1H, s).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous hydrochloric acid solution and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe crude product was crystallized from diethyl ether

출처 및 근거

ORD 기록
ord-45b8741254a24b13bb639c878acb4d03
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06500835B2

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