반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([OH:11])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.CCN(C(C)C)C(C)C.Cl.[F:34][C:35]([F:55])([F:54])[C:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([C:44]2[C:49]([C:50]([F:53])([F:52])[F:51])=[CH:48][CH:47]=[CH:46][N:45]=2)[NH2:43])=[CH:38][CH:37]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]([NH:43][C@@H:42]([C:39]1[CH:40]=[CH:41][C:36]([C:35]([F:55])([F:34])[F:54])=[CH:37][CH:38]=1)[C:44]1[C:49]([C:50]([F:51])([F:52])[F:53])=[CH:48][CH:47]=[CH:46][N:45]=1)=[O:11]참가 물질
반응물 4
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of 3-(pyridin-2-yl)propanoic acid (89 mg, 0.586 mmol, Oakwood) and DCM (4 mL) were added CDI (95 mg, 0.586 mmol) and DIPEA (0.20 mL, 1.148 mmol). After 0.5 hours, the reaction was treated with a solution of (S)-(4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (125 mg, 0.390 mmol) in DCM (1.5 mL). The solution was stirred at rt. After 4 days, the resulting product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (4 g), eluting with 0% to 60% EtOAc in hexane, to provide the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ ppm 8.79 (d, J=3.8 Hz, 1H), 8.45 (d, J=4.8 Hz, 1H), 7.96 (d, J=7.9 Hz, 1H), 7.78 (d, J=7.9 Hz, 1H), 7.44-7.52 (m, 3H), 7.34-7.43 (m, 3H), 7.03-7.12 (m, 2H), 6.63 (d, J=8.0 Hz, 1H), 3.11 (td, J=6.7 & 2.5 Hz, 2H), 2.74 (td, J=7.2 & 2.5 Hz, 2H). MS (ESI pos. ion) m/z: 454.0 (M+H).
후처리
- waitAfter 4 days
- customchromatographed through a Redi-Sep® pre-packed silica gel column (4 g)
- washeluting with 0% to 60% EtOAc in hexane
출처 및 근거
- ORD 기록
- ord-69d86137f59b4d1abca6f759140e411e
- 출처 데이터셋
- uspto-grants-2014_04
- 특허 번호
- US08710043B2
연결된 노트
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