2-Methylpyridine-4-boronic acid → N-(6-(6-chloro-5-(3-(difluoromethoxy)phenylsulfonamido)pyridin-3-yl)-3-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14](I)=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]([F:35])[F:34])[CH:27]=1)(=[O:25])=[O:24].[CH3:36][C:37]1[CH:42]=[C:41](B(O)O)[CH:40]=[CH:39][N:38]=1>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([C:41]4[CH:40]=[CH:39][N:38]=[C:37]([CH3:36])[CH:42]=4)=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH:33]([F:35])[F:34])[CH:27]=1)(=[O:25])=[O:24]Participants
Reactant 2
Product 1
Procedure
Following the procedure described in Example 44 (Step 5) N-(6-(6-chloro-5-(3-(difluoromethoxy)phenylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (114.0 mg, 180 μmol) was combined with 2-methylpyridin-4-ylboronic acid (30 mg, 216 μmol) to afford the title compound, N-(6-(6-chloro-5-(3-(difluoromethoxy)phenylsulfonamido)pyridin-3-yl)-3-(2-methylpyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide as a yellow solid. LCMS (ESI positive ion) m/z: 600.0 (M+1); 1H NMR (400 MHz, MeOH) δ ppm 2.21 (s, 3H), 2.67 (s, 3H), 6.80 (t, J=73.11 Hz, 1H), 7.35 (dd, J=8.22, 1.96 Hz, 1H), 7.47 (t, J=8.07 Hz, 1H), 7.54 (s, 1H), 7.57-7.64 (m, 1H), 7.80-7.85 (m, 1H), 7.86-7.96 (m, 2H), 8.14 (d, J=9.49 Hz, 1H), 8.57 (d, J=5.38 Hz, 1H), 8.74 (dd, J=22.45, 2.20 Hz, 2H).
Sources & evidence
- ORD record
- ord-2b9c3a313df44ee88dd9df1bfb6b20b4
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820665B2
Reaction notes
Loading…