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[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14].[CH3:18][O:19][C:20]1[N:25]=[C:24]([O:26][CH3:27])[C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][N:21]=1.ClCCl>C(OCC)(=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[C:24]([O:26][CH3:27])=[N:25][C:20]([O:19][CH3:18])=[N:21][CH:22]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH3:17])=[O:14]참가 물질
반응 조건
- 온도
- 90 °C
실험 절차
The title compound was prepared from 4-amino-8-bromo-N-ethyl-cinnoline-3-carboxamide (200.0 mg, 0.678 mmol) and 2,4-dimethoxyprimidine-5-boronic acid pinacol ester (363.1 mg, 1.362 mmol) according to Method B except that the reaction was heated at 90° C. to fully dissolve the starting materials. After 4 hours, additional 2,4-dimethoxyprimidine-5-boronic acid pinacol ester (363.1 mg, 1.362 mmol) was added and the reaction was refluxed overnignt. A third addition of 2,4-dimethoxyprimidine-5-boronic acid pinacol ester (363.1 mg, 1.362 mmol) and an additional 5 mol % tetrakis(triphenylphospine)palladium(0) were required to force the reaction to completion. The reaction was then worked up as described in Method B using dichloromethane rather than ethyl acetate for the extraction and crystallizing the material obtained from the flash column from chloroform/hexanes to afford the title compound as a white solid (89.5 mg, 37%). 1H NMR (300.132 MHz, CDCl3) δ 8.47 (s, 1H), 8.32 (s, 1H), 7.90 (dd, J=7.6, 2.1 Hz, 1H), 7.78-7.70 (m, 2H), 4.07 (s, 3H), 3.93 (s, 3H), 3.53 (dq, J=5.7, 7.3 Hz, 2H), 1.28 (t, J=7.3 Hz, 3H). MS APCI, m/z=354 (M+H). HPLC 2.07 min.
후처리
- dissolutionto fully dissolve the starting materials
- temperaturethe reaction was refluxed overnignt
- customthe reaction to completion
- extractionfor the extraction
- customcrystallizing the material
출처 및 근거
- ORD 기록
- ord-f640dd042e704a8d9faade1ec2e1bb8d
- 출처 데이터셋
- uspto-grants-2008_12
- 특허 번호
- US07465795B2
연결된 노트
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