3,4-diamino-N-quinolin-2-yl-benzamide → 2-(2,6-Dichloro-4-dimethylcarbamoylmethoxyphenyl)-3H-benzoimidazole-5-carboxylic acid quinolin-2-ylamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[Cl:22][C:23]1[CH:24]=[C:25]([CH:33]=[C:34]([Cl:38])[C:35]=1[CH:36]=O)[O:26][CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29]>>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[NH:7][C:5]([C:4]1[CH:18]=[CH:19][C:20]2[N:21]=[C:36]([C:35]3[C:34]([Cl:38])=[CH:33][C:25]([O:26][CH2:27][C:28](=[O:29])[N:30]([CH3:31])[CH3:32])=[CH:24][C:23]=3[Cl:22])[NH:1][C:2]=2[CH:3]=1)=[O:6]Participants
3
Procedure
The title compound was prepared from 3,4-diamino-N-quinolin-2-yl-benzamide (from Example 6-17) and 2-(3,5-dichloro-4-formylphenoxy)-N,N-dimethyl-acetamide analogous to Example 6-17. 1H NMR (Methanol-d4, 400 MHz): δ 8.83 (d, 1H), 8.56 (d, 1H), 8.20 (t, 1H), 8.18 (t, 1H), 8.14 (d, 1H), 8.02 (m, 2H), 7.90 (d, 1H), 7.79 (t, 1H), 7.28 (s, 2H), 5.02 (s, 2H), 3.09 (s, 3H), 3.01 (s, 3H). MS (m/z) 534.2 (M+1); Retention time: 1.28 min (Method 10).
Sources & evidence
- ORD record
- ord-e4fc7030e04a46f9896c57c0d787c51e
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222248B2
Reaction notes
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