2-Aminobenzenesulfonamide → N-[2-(aminosulfonyl)phenyl]-1-benzyl-4-hydroxy-2-oxo-6-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxamide
Reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][N:16]=2)[C:11]([OH:24])=[C:10]([C:25](OCC)=[O:26])[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C2C(=CC=CN=2)C(O)=C(C(OCC)=O)C1=O)C1C=CC=CC=1.[NH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[S:62]([NH2:65])(=[O:64])=[O:63].NC1C=CC(Br)=CC=1S(N)(=O)=O>>[NH2:65][S:62]([C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=1[NH:55][C:25]([C:10]1[C:9](=[O:30])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[C:12]([C:11]=1[OH:24])=[CH:13][C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:15][N:16]=2)=[O:26])(=[O:63])=[O:64]Participants
5
Reactant 4
Product 1
Procedure
The title compound was prepared according to the procedure of Example 84C substituting ethyl 1-benzyl-6-phenyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate for the product of Example 84B and substituting 2-amino-benzenesulfonamide for the product of Example 84A. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.72 (s, 2 H) 7.28 (m, 6 H) 7.44 (m, 2 H) 7.54 (m, 3 H) 7.67 (m, 1 H) 7.85 (d, J=6.99 Hz, 2 H) 7.92 (dd, J=8.09, 1.47 Hz, 1 H) 7.99 (d, J=8.09 Hz, 1 H) 8.70 (d, J=2.21 Hz, 1 H) 9.17 (d, J=2.21 Hz, 1 H) 12.41 (s, 1 H) 16.80 (s, 1 H).
Sources & evidence
- ORD record
- ord-d1e980eb9b354ab5a7edc98640e46011
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902203B2
Reaction notes
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