Hydrochloric Acid → HCID 12132336, compound

Ethane thiol (0.45 mL, 6.08 mmol) was added to lithium metal (14 mg, 2.02 mmol), and the mixture was stirred for one hour at room temperature. To tire mixture were then added dry DMF (5 mL) and 2-(3-cyano-4-isobutyloxyphenyl)-7-methoxy-1,3-benzothiazole (150 mg, 0.44 mmol). The resulting mixture was stirred at 80° C. for 8.5 hours, cooled to room temperature, and, after addition of icewater (10 mL), made to pH 7 by addition of aqueous 1M hydrochloric acid. The mixture was then extracted with ethyl acetate (20 mL). The ethyl acetate portion was washed successively with water (10 mL) and aqueous saturated brine (10 mL), dried over anhydrous sodium sulfate, and placed under reduced pressure to distill the solvent off. The residue was purified by silica, gel column chromatography (ethyl acetate/hexane=1/3), and suspended in hexane. The obtained crystalline product was collected by filtration, washed with hexane, and dried in air, to give 17 mg (yield 12%) of the desired compound in the form of a pale yellow crystalline product.

1. stirringThe resulting mixture was stirred at 80° C. for 8.5 hours
2. temperaturecooled to room temperature
3. additionafter addition of icewater (10 mL)
4. extractionThe mixture was then extracted with ethyl acetate (20 mL)
5. washThe ethyl acetate portion was washed successively with water (10 mL) and aqueous saturated brine (10 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. distillationto distill the solvent off
8. customThe residue was purified by silica, gel column chromatography (ethyl acetate/hexane=1/3)
9. filtrationThe obtained crystalline product was collected by filtration
10. washwashed with hexane
11. customdried in air

ORD record

ord-57797fc9e17c415ea494fb65c7c55a66

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253154B2