Dimethylacetamide → N-{6-chloro-2-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

Temperature

90 °C

A mixture of 6-chloro-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.60 g), bromomalonaldehyde (0.38 g) and N,N-dimethylacetamide (10 ml) was stirred at 90° C. for 3 hr. Water was added to the reaction mixture, and the resulting crystals were collected by filtration, washed with water, and dried. To a mixture of the obtained crystals, tetrahydrofuran (10 ml) and methanol (5 ml) was added sodium borohydride (70 mg) at 0° C., and the mixture was stirred at the same temperature for 30 min. 10% Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (0.38 g, yield 54%) as pale-yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). melting point 214-215° C.

1. filtrationthe resulting crystals were collected by filtration
2. washwashed with water
3. customdried
4. additionTo a mixture of the obtained crystals, tetrahydrofuran (10 ml) and methanol (5 ml)
5. additionwas added sodium borohydride (70 mg) at 0° C.
6. stirringthe mixture was stirred at the same temperature for 30 min
7. addition10% Aqueous citric acid solution was added to the reaction mixture
8. extractionthe mixture was extracted with ethyl acetate
9. washThe ethyl acetate layer was washed with saturated brine
10. dry with materialdried (MgSO4)
11. concentrationconcentrated

ORD record

ord-95ab31f1aa5848d1adbb0f9b6eb5e8d1

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07777047B2