4-Chlorobenzylamine → N-(4-chlorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

A solution of ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (627 mg, 2.23 mmol), 4-chlorobenzylamine (2.0 mL, 16.4 mmol), 0.5 M sodium methoxide in methanol (25 mL, 8.92 mmol) and methanol (10 mL) was stirred under nitrogen in a tightly capped 250 mL round bottom flask at 50° C. for 24 hours. The initial solution slowly dropped a thick white precipitate during the reaction. After cooling to room temperature, the mixture was filtered, and the collected solid was washed with methanol and dried in vacuo, leaving a white solid. The crude solid was suspended in boiling methanol (200 mL), cooled to room temperature, and filtered, to give the title compound as a white powder (585 mg).

1. customduring the reaction
2. filtrationthe mixture was filtered
3. washthe collected solid was washed with methanol
4. customdried in vacuo
5. customleaving a white solid
6. temperaturecooled to room temperature
7. filtrationfiltered

ORDレコード

ord-9e59478c9ad84d828ec914ab1d191438

出典データセット

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06852731B2