Oxalyl chloride → 2-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)-5-iodobenzamide

To a stirring solution of 1-Boc-isonipecotic acid (15.26 g, 66.55 mmol) in methanol (135 mL) was added sodium methoxide (3.8 g, 66.8 mmol). After stirring for 1 h, the solvent was removed in vacuo. A portion of the residue (8.92 g, 35.5 mmol) was suspended in dichloromethane (95 mL) and oxalyl chloride (4 mL, 45 mmol) was added, followed by a couple of drops of N,N-dimethylformamide. After stirring for 1 h, the solvent was removed in vacuo. The residue was suspended in dichloromethane (45 mL) and added to a solution of 2-amino-N-(5-chloropyridin-2-yl)-5-iodobenzamide (8.86 g, 23.7 mmol), N,N-diisopropylethylamine (5 mL, 28 mmol), and 4-(N,N-dimethylamino)pyridine (0.33 g, 2.7 mmol) in dichloromethane (50 mL). After stirring 19 h, the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was slurried in diethyl ether and filtered to give 8.6 g (62%) of a pink solid.

1. customthe solvent was removed in vacuo
2. stirringAfter stirring for 1 h
3. customthe solvent was removed in vacuo
4. stirringAfter stirring 19 h
5. customthe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
6. dry with materialThe organic phase was dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. filtrationfiltered

ORDレコード

ord-961d5d32bcab4ca9ab16422c7d2bda17

出典データセット

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06759414B2