Ethanol → HCID 135834141, 화합물

HRID 1017724노트

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HRID 1017724 반응식
[CH:1]([C:3]1[C:8](OC)=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12](=[O:18])OC(C)(C)C)=O.[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[CH2:28]C(OCC)=O.N1CCCCC1.[CH2:40]([OH:42])C>>[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[C:28]1[C:12](=[O:18])[NH:11][C:4]2[C:3]([CH:1]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[O:42][CH3:40]

참가 물질

5

반응물 4

HCID 702EthanolHCID 8082PiperidineHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 22897235HCID 22897235, 화합물

생성물 1

HCID 135834141HCID 135834141, 화합물

실험 절차

A solution of tert-butyl 2-formyl-3-methoxyphenylcarbamate (13-1, 0.50 g, 1.9 mmol, 1 equiv, prepared by the formylation method utilized in the examples above), ethyl 1H-benzimidazol-2-ylacetate (0.39 g, 1.9 mmol, 1.0 equiv, prepared by the method of Rahmouni, M, Derdour, A., Bazureau, J., and Hamelin Tetrahedron Lett. 1994, 35, 4563-4564), and piperidine (0.090 mL, 0.91 mmol, 0.48 equiv) in ethanol (50 mL) was heated at reflux for 20 h. The reaction mixture was cooled and the precipitate which formed was filtered and air dried to give 3-(1H-benzimidazol-2-yl)-8-methoxy-2(1H)-quinolinone (13-2). 1H NMR (400 MHz, DMSO-d6) δ 12.59 (s, 1H), 12.43 (s, 1H), 9.25 (s, 1H), 7.71 (m, 1H), 7.66 (m, 1H), 7.55 (t, 1H, J=8.2 Hz), 7.20 (m, 2H), 7.03 (d, 1H, J=8.2 Hz), 6.85 (d, 1H, J=8.2 Hz).

후처리

  1. customprepared by the method of Rahmouni, M, Derdour
  2. temperatureat reflux for 20 h
  3. temperatureThe reaction mixture was cooled
  4. customthe precipitate which formed
  5. filtrationwas filtered
  6. customair dried

출처 및 근거

ORD 기록
ord-9fc2e3f719dd4c25a1bd6ccf7b67a8fc
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479512B1

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