Methyl 3-(3,5-dimethyl-4-formylphenyl)propionate → 3-{4-[6-(5,6-Dimethylpyridin-2-ylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-propionic acid
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[N:9]=1)=[O:6].C[O:21][C:22](=[O:35])[CH2:23][CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([CH:32]=O)=[C:27]([CH3:34])[CH:26]=1>>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5]([C:4]2[CH:16]=[CH:17][C:18]3[N:19]=[C:32]([C:28]4[C:27]([CH3:34])=[CH:26][C:25]([CH2:24][CH2:23][C:22]([OH:35])=[O:21])=[CH:30][C:29]=4[CH3:31])[NH:1][C:2]=3[CH:3]=2)=[O:6])=[N:9][C:10]=1[CH3:15]Participants
3
Procedure
The title compound was prepared from 3,4-diamino-N-(5,6-dimethylpyridin-2-yl)-benzamide and 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester (from Example 6-17) analogous to the final two steps of Example 6-17. 1H-NMR (DMSO-d6, 400 MHz): δ 10.58 (s, 0.5H), 10.53 (s, 0.5H), 8.41 (s, 0.5H), 8.23 (s, 0.5H), 7.92 (m, 2.5H), 7.72 (d, J=8.6 Hz, 0.5H), 7.56 (m, 2H), 7.08 (s, 2H), 2.84 (t, J=7.4 Hz, 2H), 2.58 (t, J=7.4 Hz, 2H), 2.41 (s, 3H), 2.24 (s, 3H), 2.09 (s, 6H). MS (m/z) 392.3 (M−1); Retention time=1.09 min (Method 10).
Sources & evidence
- ORD record
- ord-f87d71b086494b28af9831393f33ff9b
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222248B2
Reaction notes
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