1-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanol → 1-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanone

HRID 340303노트

반응식

HRID 340303 반응식
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH:16]([OH:18])[CH3:17])=[CH:15][C:4]=2[N:3]=1>C(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([C:16](=[O:18])[CH3:17])=[CH:15][C:4]=2[N:3]=1

참가 물질

4

반응물 1

HCID 582136971-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanol

생성물 1

HCID 582135271-(5-Aminobenzo[f][1,7]naphthyridin-8-yl)ethanone

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution 1-(5-aminobenzo[f][1,7]naphthyridin-8-yl)ethanol (from Example 88) (1.0 eq.) and activated MnO2 (20 eq.) in DCM (0.1 M) was stirred at ambient temperature over night. The reaction mixture was diluted with DCM. The MnO2 was filtered off, and the filtrate was concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give 1-(5-aminobenzo[f][1,7]naphthyridin-8-yl)ethanone as a yellow solid: 1H NMR (acetone-d6): δ 9.11 (dd, 1H), 8.99 (dd, 1H), 8.56 (d, 1H), 8.20 (d, 1H), 7.94-7.88 (m, 2H), 6.90 (br s, 2H), 2.70 (s, 3H). LRMS [M+H]=238.1.

후처리

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe filtrate was concentrated en vacuo
  3. customto obtain a crude residue
  4. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-161c795cbcab45a4973f552c889a6a17
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895577B2

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