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Acetic Anhydride → N-[2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylamino]-ethyl]-acetamide

HRID 1861006
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인쇄 미리보기

반응식

HRID 1861006 반응식
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)[C:9]2[C:10](=[O:19])[NH:11][C:12]3[C:17]=2[C:16]=1[C:15]([F:18])=[CH:14][CH:13]=3.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(CC)CC)C>C(Cl)Cl>[F:18][C:15]1[C:16]2[C:17]3[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:19])[C:9]=3[C:8]([C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)=[CH:7][C:6]=2[NH:5][CH2:4][CH2:3][NH:2][C:25](=[O:27])[CH3:26]
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참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 101323945-(2-amino-ethyl amino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one hydrochloride salt

생성물 1

HCID 10132679N-[2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylamino]-ethyl]-acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 5-(2-amino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one hydrochloride salt (from Example 10 above) (35.5 mg, 0.1 mmol) in CH2Cl2 (2 mL) were added acetic anhydride (Fisher Scientific, 10.2 mg, 0.1 mmol) and triethylamine (Aldrich, 20.2 mg, 0.2 mmol) at room temperature. The reaction mixture was stirred for 2 hours at the same temperature and then quenched with a saturated aqueous ammonium chloride solution (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were successively washed with water (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate and hexanes, filtered, and dried to give N-[2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylamino]-ethyl]-acetamide as a brown solid. (Yield 13.5 mg, 38.4%).

후처리

  1. customquenched with a saturated aqueous ammonium chloride solution (5 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic extracts were successively washed with water (5 mL) and brine (5 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated with ethyl acetate and hexanes
  8. filtrationfiltered
  9. customdried

출처 및 근거

ORD 기록
ord-7b77352872654df3bfa2f9a98802c1a4
출처 데이터셋
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06531598B1

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