Reaktionsgleichung
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][CH3:18])[C:11]=2[CH:15]=O)[CH:6]=1)=[O:4].Cl.[NH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1>>[NH2:31][S:28]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][NH:20][CH2:15][C:11]2[C:10]([O:17][CH3:18])=[CH:9][CH:8]=[C:7]3[C:12]=2[CH:13]=[CH:14][C:5]([C:3]([OH:2])=[O:4])=[CH:6]3)=[CH:27][CH:26]=1)(=[O:29])=[O:30]Komponenten
Versuchsvorschrift
The title compound was prepared as a white solid (0.245 g, 34% for two steps) from 6-methoxy-5-formyl-2-naphthoic acid methyl ester using p-aminomethyl-benzenesulfonamide hydrochloride and a procedure similar to steps 3-4 of Example 1, mp 283-285° C. (decomp.); 1H NMR (DMSO-d6) δ3.94 (s, 3H), 4.37 (s, 2H), 4.53 (s, 2H), 7.46 (s, 2H), 7.60 (d, J=9.2 Hz, 1H), 7.77 (d, J=8.2 Hz, 2H), 7.90 (d, J=8.2 Hz, 2H), 8.01 (dd, J=1.4, 9.0 Hz, 1H), 8.16 (d, J=9.0 Hz, 1H), 8.28 (d, J=9.2 Hz, 1H), 8.61 (s, 1H), 9.25-9.46 (bs, 2H), 12.78-13.18 (bs, 1H); IR (neat) 2380-3300, 1670, 1625, 1600, 1485, 1470, 1455, 1430, 1420, 1325, 1310, 1285, 1265, 1220, 1185, 1165, 1105, and 1040 cm−1; mass spectrum [(+) ESI], m/z401 (M+H)+ and [(−) ESI], m/z 399 (M−H)−; Anal. Calcd. for C20H20N2O5S.HCl: C, 54.98; H, 4.84; N, 6.41, Found: C, 54.60; H, 4.93; N, 6.17.
Quellen und Nachweise
- ORD-Eintrag
- ord-4b57ae59a45345b9884b6cdbd148052e
- Quelldatensatz
- uspto-grants-2005_02
- Patentnummer
- US06849761B2
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