1,3-Thiazole-5-carbaldehyde → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

In 1,2-dichloroethane (15 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-benzazepine-4-carboxylate (0.50 g). To the solution were added 1,3-thiazole-5-carbaldehyde 10.43 g) and sodium triacetoxyborohydride (0.80 g), and the mixture was stirred at room temperature for 24 hours. To the mixture was added sodium triacetoxyborohydride (0.27 g), and the mixture was stirred for 6 hours. The solvent was removed under reduced pressure, the resulting residue was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/2→2/3) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.50 g).

1. stirringthe mixture was stirred for 6 hours
2. customThe solvent was removed under reduced pressure
3. additionthe resulting residue was added to water
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried with magnesium sulfate
7. customThe solvent was removed under reduced pressure
8. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/2→2/3)

ORD 기록

ord-20fab3757f764e6cb93121b37c4e138d

출처 데이터셋

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06936602B1