4-(1H-imidazol-2-yl)benzoic Acid → 3-{[4-(1H-Imidazol-2-yl)-benzoylamino]-methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester
Reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:10][CH:11]=2)[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]=1[C:25]([O:27][CH3:28])=[O:26].[NH:29]1[CH:33]=[CH:32][N:31]=[C:30]1[C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1>>[CH3:28][O:27][C:25]([C:5]1[N:6]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:7]2[C:12]([C:13](=[O:14])[C:4]=1[CH2:3][NH:2][C:38](=[O:39])[C:37]1[CH:36]=[CH:35][C:34]([C:30]3[NH:31][CH:32]=[CH:33][N:29]=3)=[CH:42][CH:41]=1)=[CH:11][CH:10]=[C:9]([C:15]([F:16])([F:17])[F:18])[N:8]=2)=[O:26]Participants
3
Reactant 2
Product 1
Procedure
3-{[4-(1H-Imidazol-2-yl)-benzoylamino]-methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester was prepared starting from intermediate J and 4-(1H-imidazol-2-yl)-benzoic acid. 1H NMR (DMSO-d6) δ ppm 8.90 (d, J=8.1 Hz, 1H) 8.77 (t, J=4.6 Hz, 1H) 7.91-8.00 (m, 3H) 7.83-7.89 (m, 2H) 7.52-7.59 (m, 3H) 7.47 (s, 2H) 7.43 (dd, J=6.7, 2.7 Hz, 2H) 4.46 (d, J=4.8 Hz, 2H) 3.40 (s, 3H). MS calcd. for C28H20F3N5O4 [(M+H)+] 548.1, obsd. 548.1.
Sources & evidence
- ORD record
- ord-5cde166bf5be41cdb696d234935eefba
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501732B2
Reaction notes
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