Diisopropylethylamine → N-(4-chlorobenzyl)-2-{[[2-hydroxy-2-(4-methoxyphenyl)ethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

温度

60 °C

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (80 mg, 0.20 mmol), 1-(4-methoxyphenyl)-2-(methylamino)ethanol (Tetrahedron 1999, 55, 4831-4842) (58 mg, 0.32 mmol) and diisopropylethylamine (67 μL, 0.38 mmol) in dry DMF (5 mL) was heated to 60° C., becoming a solution. The reaction was stirred for 16 hours at that temperature. After cooling to room temperature, the solution was diluted with water (15 mL). The resulting milky suspension was stirred vigorously for 30 minutes, and then left standing overnight at room temp. The mixture was filtered, and the collected solid was washed with water and dried in vacuo, leaving a white solid. Recrystallization from acetonitrile (10 mL, dissolved with warming and then cooled to 0° C. overnight) gave the title compound (49 mg) as a white solid.

1. temperatureAfter cooling to room temperature
2. stirringThe resulting milky suspension was stirred vigorously for 30 minutes
3. waitleft
4. waitstanding overnight at room temp
5. filtrationThe mixture was filtered
6. washthe collected solid was washed with water
7. customdried in vacuo
8. customleaving a white solid
9. customRecrystallization from acetonitrile (10 mL
10. dissolutiondissolved
11. temperaturewith warming
12. temperaturecooled to 0° C. overnight)

ORDレコード

ord-7a781d34d2dd465a8bb5c917e4b4912b

出典データセット

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06852731B2