Diethyl Ether → 3-Chloro-N-{2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide

To a stirred solution of 2,6-dimethyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (Description 4) (100 mg, 0.352 mmol) in THF (2 mL), cooled in an ice bath, was added LiHMDS (1M solution in THF) (0.774 mL, 0.774 mmol). The reaction mixture was stirred at RT for 1 h before the addition of 3-chlorobenzenesulfonyl chloride (0.124 mL, 0.879 mmol). The reaction mixture was then stirred at RT for a further 12 h. The reaction mixture was then diluted with water (15 mL) and the aqueous layer extracted with DCM (3×30 mL). The combined organic extracts were dried over a phase separating column and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, afforded a solid which was dissolved in the minimum amount of DCM. Upon addition of diethyl ether, a solid precipitated out which was collected by filtration, washed with diethyl ether and dried, to afford the title compound (89 mg). LCMS (A) m/z: 459 [M+1]+, Rt 1.03 min (basic).

1. extractionthe aqueous layer extracted with DCM (3×30 mL)
2. customThe combined organic extracts were dried over a phase
3. customseparating column
4. concentrationconcentrated
5. customPurification by chromatography on silica gel
6. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane
7. customafforded a solid which
8. customa solid precipitated out which
9. filtrationwas collected by filtration
10. washwashed with diethyl ether
11. customdried

ORD-Eintrag

ord-2b17ec6c7ebb4237aac996d30365ab89

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09029545B2