Cyclopropanecarbonyl chloride → HCID 59454505, 화합물

HRID 455215노트

반응식

HRID 455215 반응식
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]3[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=3)[C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1>N1C=CC=CC=1>[CH:34]1([C:37]([NH:1][C:2]2[S:3][C:4]3[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([O:14][C:15]4[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=4)[C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=4)=[O:19])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:38])[CH2:36][CH2:35]1

참가 물질

4

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 866446963-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]-N-[3-(trifluoromethyl)phenyl]benzamide

생성물 1

HCID 59454505HCID 59454505, 화합물수율 42.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 3-[(2-amino-7-nitro-1,3-benzothiazol-6-yl)oxy]-N-[3-(trifluoromethyl)phenyl]benzamide (200 mg, 0.421 mmol) in pyridine (4 mL) was added cyclopropanecarbonyl chloride (76 μL, 0.842 mmol), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (50 ml), washed successively with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=40/60→100/0), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (97 mg, 42%) as a pale-yellow powder.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate (50 ml)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=40/60→100/0)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-064eeea8851a43709e9ea76ca3f5cc85
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497274B2

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