2-Amino-5-methylpyridine → 4-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-2-methyl-N-(5-methylpyridin-2-yl)benzofuran-6-carboxamide
Reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([O:14]CC)=O)[CH:3]=1.[F:17][C:18]1[CH:28]=[C:27](F)[CH:26]=[CH:25][C:19]=1[C:20]([N:22]([CH3:24])[CH3:23])=[O:21].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][N:32]=1>>[CH3:23][N:22]([CH3:24])[C:20]([C:19]1[CH:25]=[CH:26][C:27]([O:1][C:2]2[C:7]3[CH:8]=[C:9]([CH3:11])[O:10][C:6]=3[CH:5]=[C:4]([C:12]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][N:32]=3)=[O:14])[CH:3]=2)=[CH:28][C:18]=1[F:17])=[O:21]Participants
4
Procedure
The title compound was prepared in a similar manner as described for Example 271, from ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (0.275 g, 1.25 mmol), 2,4-difluoro-N,N-dimethylbenzamide (0.289 g, 1.56 mmol) and 2-amino-5-methylpyridine (0.229 g, 2.1 mmol) in two steps to give an off-white solid (131 mg, 24% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.79 (s, 1 H) 8.21 (m, 1 H) 8.16 (s, 1 H) 8.06-8.08 (d, 1 H)) 7.66 (m, 1 H) 7.64 (m, 1 H) 7.37-7.41 (t, 1 H) 7.02-7.06 (m, 1 H) 6.89-6.92 (m, 1 H) 6.50 (s, 1 H) 2.99 (s, 3 H) 2.87 (m, 3 H) 2.47 (m, 3 H) 2.27 (s, 3 H).
Sources & evidence
- ORD record
- ord-63eb572210f54e2fafc427652e7699d3
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842713B2
Reaction notes
Loading…