1-Hydroxybenzotriazole → Butyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate

反応式

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:23])[NH:21][CH3:22])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]([OH:26])=[O:25])=[CH:5][CH:4]=1.[CH:27]1[CH:28]=CC2N(O)N=N[C:31]=2[CH:32]=1>CN(C1C=CN=CC=1)C.C(O)CCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:23])[NH:21][CH3:22])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:24]([O:26][CH2:28][CH2:27][CH2:32][CH3:31])=[O:25])=[CH:5][CH:4]=1

参加物

実験手順

To a suspension of 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)-quinoline-3-carboxylic acid (0.1 g) in dichloromethane EDC.HCl (1-Ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride, 0.161 g), HOBt (N-hydroxybenzotriazole 0.042 g), DMAP (4-dimethylaminopyridine, 0.17 g) and n-butanol (25 mL) were added, and the reaction mixture was stirred at room temperature for 3 hours. After aqueous work up, the reaction mixture was extracted, concentrated and dried over anhydrous sodium sulphate to afford the crude product which was later purified by column chromatography to afford 0.05 g (55% yield) of butyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ 10.84 (s, 1H, —NH—), 9.21 (s, 1H, aromatic), 8.05 (d, 1H, J=8.8 Hz, aromatic), 7.97 (d, 1H, J=8.8 Hz, aromatic), 7.80 (s, 1H, aromatic), 7.16 (d, 2H, J=8.7 Hz, aromatic), 6.96 (d, 2H, J=8.7 Hz, aromatic), 5.60 (s, 1H, —NHCH3—), 4.41 (t, 2H, J=6.6 Hz, —O—CH2—), 3.87 (s, 3H, —OCH3), 2.88 (s, 3H, —NCH3), 1.92-1.75 (m, 2H, —O—CH2—CH2—CH2—), 1.65-1.46 (m, 2H, —O—CH2—CH2—CH2—), 1.12-0.98 (m, 3H, —CH3); LC-MS (m/z) 407.9 (M+1).