Sodium Bicarbonate → N-(3-fluoro-4-(3-(1-methylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide
반응식
[NH2:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[N:13](CC4C=CC(OC)=CC=4)[N:14]=[C:15]([NH:16][CH:17]4[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)[C:8]=23)=[C:4]([F:35])[CH:3]=1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]2[C:48](=[O:49])[C:47]([C:50](O)=[O:51])=[CH:46][CH:45]=[N:44]2)=[CH:39][CH:38]=1.C([O-])(O)=O.[Na+]>>[F:35][C:4]1[CH:3]=[C:2]([NH:1][C:50]([C:47]2[C:48](=[O:49])[N:43]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)[N:44]=[CH:45][CH:46]=2)=[O:51])[CH:34]=[CH:33][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:13][N:14]=[C:15]([NH:16][CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[C:8]=12참가 물질
반응물 3
생성물 1
실험 절차
Prepared by a 2-step process from 4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-N-(1-methylpiperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-3-amine and 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (prepared as in Example 19, Step C) according to the procedure described for Example 21, Steps A and B, except that the crude was treated with aqueous NaHCO3). The crude was rinsed with Et2O to afford 34 mg (96%) of the desired product. LRMS (ESI pos) m/e 573.0 (M+1). 1H-NMR (400 MHz, CDCl3/CD3OD) δ 8.39 (d, 1H), 8.32 (d, 1H), 8.14 (d, 1H), 8.03 (dd, 1H), 7.66 (m, 2H), 7.48 (m, 1H), 7.39 (t, 1H), 7.28 (t, 2H), 6.12 (d, 1H), 3.76 (m, 1H), 3.25 (m, 2H), 2.51 (m, 2H), 2.46 (s, 3H), 2.25 (m, 2H), 1.73 (m, 2H); 19F-NMR (376 MHz, CDCl3/CD3OD) δ −113.8, −128.4.
후처리
- washThe crude was rinsed with Et2O
출처 및 근거
- ORD 기록
- ord-e94140511f744c5eba99bc09ab021e0a
- 출처 데이터셋
- uspto-grants-2010_05
- 특허 번호
- US07723330B2
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