Reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH2:18][C:19]([O:21]C)=[O:20])[C:11]=2[CH:15]=O)[CH:6]=1)=[O:4].[F:23][C:24]([F:35])([F:34])[O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>>[C:19]([CH2:18][O:17][C:10]1[C:11]([CH2:15][NH:31][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][C:24]([F:23])([F:34])[F:35])=[CH:27][CH:28]=2)=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:14]=[CH:13]2)([OH:21])=[O:20]Participants
Procedure
The title compound was prepared as a white solid (0.050 g, 58% for two steps) from 6-methoxycarbonylmethoxy-5-formyl-2-naphthoic acid methyl ester using 4-trifluoromethoxy-benzyl amine and a procedure similar to steps 3-4 of Example 1, mp >266° C. (decomp.); 1H NMR (DMSO-d6) δ4.31 (s, 2H), 4.58 (s, 2H), 4.77 (s, 2H), 7.42 (d, J=8.4 Hz, 2H), 7.62 (d, J=9.3 Hz,1 H), 7.68 (d, J=8.7 Hz, 2H), 8.00 (dd, J=1.5, 8.9 Hz, 1H), 8.17 (d, J=9.0 Hz, 1H), 8.21 (d, J=9.3 Hz, 1H), 8.58 (d, J=1.2 Hz, 1H), 10.05-10.54 (bs, 1H), 12.74-13.46 (bs, 1H); IR (neat) 2450-3200, 1695, 1630, 1600, 1575, 1510, 1485, 1440, 1310, 1265, 1215, 1170, and 1110 cm−1; mass spectrum [(+) ESI], m/z 450 (M+H)+ and [(−) ESI], m/z 448 (M−H)−; Anal. Calcd. for C22H18F3NO6.1.0H2O: C, 56.54; H, 4.31; N, 3.00, Found: C, 56.16; H, 4.26; N, 2.86.
Sources & evidence
- ORD record
- ord-fb76dbe7ad0a4f989af905fde65a2cc3
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06849761B2
Linked notes
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