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

Temperatur

80 °C

A mixture of 7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (1.00 g), bromomalonaldehyde (0.86 g) and N,N-dimethylacetamide (8 ml) was stirred at 80° C. for 3 hr. Water was added to the reaction mixture, and the resulting crystals were collected by filtration, washed with water, and dried. The obtained crystals were dissolved in tetrahydrofuran (8 ml) and methanol (8 ml), sodium borohydride (63 mg) was added at 0° C., and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were collected by filtration, washed with water, and dried. The crystals were subjected to silica gel column chromatography to give the title compound (0.43 g, yield 39%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio). melting point 201-202° C.

1. filtrationthe resulting crystals were collected by filtration
2. washwashed with water
3. customdried
4. dissolutionThe obtained crystals were dissolved in tetrahydrofuran (8 ml)
5. additionmethanol (8 ml), sodium borohydride (63 mg) was added at 0° C.
6. stirringthe mixture was stirred at 0° C. for 1 hr
7. concentrationThe reaction mixture was concentrated
8. addition10% aqueous citric acid solution was added
9. filtrationthe resulting crystals were collected by filtration
10. washwashed with water
11. customdried

ORD-Eintrag

ord-f0bba37938ad433c8130e84fd8724705

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07652133B2