N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide → 1-benzyl-3-(1,1-dioxido-4H-pyrido[3,2-e][1,2,4]thiadiazin-3-yl)-4-hydroxy-1,8-naphthyridin-2(1H)-one
Reaction equation
[NH2:1][S:2]([C:5]1[C:10]([NH:11][C:12]([C:14]2[C:15](=[O:32])[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[C:22]([C:23]=2[OH:24])=[CH:21][CH:20]=[CH:19][N:18]=3)=O)=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:4])=[O:3].NS(C1C=C(Br)C=CC=1NC(C1C(=O)N(CC2C=CC=CC=2)C2C(C=1O)=CC=CN=2)=O)(=O)=O>>[CH2:25]([N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][N:18]=2)[C:23]([OH:24])=[C:14]([C:12]2[NH:11][C:10]3[CH:9]=[CH:8][CH:7]=[N:6][C:5]=3[S:2](=[O:4])(=[O:3])[N:1]=2)[C:15]1=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared according to the procedure of Example 84D substituting the product of Example 100A for the product of Example 84C to give after purification by reverse phase HPLC (water/acetonitrile/0.1% NH4OAc gradient) the title compound as a white solid (0.053 g, 10%). MS (ESI−) m/z 432 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 5.70 (m, 2H), 7.25 (m, 7H), 7.50 (dd, J=7.91, 4.60 Hz, 1H), 7.80 (dd, J=8.46, 4.41 Hz, 1H), 8.17 (d, J=8.46 Hz, 1H), 8.60 (m, J=5.79, 1.88, 1.88 Hz, 1H), 8.68 (dd, J=4.41, 1.10 Hz, 1H), 8.82 (dd, J=4.78, 1.84 Hz, 1H).
Workup
- customto give
- customafter purification by reverse phase HPLC (water/acetonitrile/0.1% NH4OAc gradient) the title compound as a white solid (0.053 g, 10%)
Sources & evidence
- ORD record
- ord-842ad780ed174ab5b35bd50bbdf4ca79
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902203B2
Reaction notes
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