Pyridine → Methyl 2-(4-(propylcarbamoyl)phenylcarbamoyl)isoindoline-5-carboxylate

関与物質

反応手順

A solution of 4-amino-N-propylbenzamide (390 mg, 2.19 mmol), bis(2,5-dioxopyrrolidin-1-yl) carbonate (700 mg, 2.74 mmol), and pyridine (0.18 mL, 2.19 mmol) in acetonitrile (5 mL) was stirred at ambient temperature for 30 minutes. Diisopropylethylamine (0.85 mL, 6.6 mmol)) was added followed by a suspension of methyl isoindoline-5-carboxylate hydrochloride (538 mg, 2.52 mmol) and diisopropylethylamine (0.46 mL, 4.4 mmol) in 1-methyl-2-pyrrolidinone (8 mL) added dropwise via syringe over ˜5 minutes. The reaction became a suspension and was stirred 3 hours. The reaction was treated with water (30 mL) and the resulting suspension was stirred 5 minutes and filtered. The solid collected was washed with water and dried under vacuum to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.63 (s, 1H), 8.26 (t, J=5.6 Hz, 1H), 7.94-7.97 (m, 1H), 7.90-7.96 (m, 1H), 7.75-7.78 (m, 2H), 7.63-7.67 (m, 2H), 7.52 (d, J=7.9 Hz, 1H), 4.83-4.86 (m, 4H), 3.87 (s, 3H), 3.16-3.22 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 382 (M+H)+.

情報源と証拠