Triethylamine → 1-[2-(1-Cyclobutyl-piperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]-propan-1-one

A solution of 2-(1-Cyclobutyl-piperidin-4-yloxy)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine (1.3 grams, 4 mmol, obtained in above step) and triethylamine (1.9 mL, 13 mmol) in dichloromethane (30 mL) was cooled to 0° C. Propionylchloride (0.4 mL, 5 mmol) in dichloromethane (5 mL) was added drop wise over a period of 15 minutes and stirred the reaction for 30 minutes. Reaction mass was poured onto ice cold water and the product was extracted with ethyl acetate (3×50 mL). Combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. Organic volatiles were evaporated under vacuum. The residue was purified by flash chromatography (methanol/chloroform, 2/98) to obtain the title compound (1.0 gram).

1. customthe reaction for 30 minutes
2. customReaction mass
3. additionwas poured onto ice cold water
4. extractionthe product was extracted with ethyl acetate (3×50 mL)
5. washCombined organics were washed with water
6. dry with materialdried over anhydrous sodium sulphate
7. customOrganic volatiles were evaporated under vacuum
8. customThe residue was purified by flash chromatography (methanol/chloroform, 2/98)

ORD-Eintrag

ord-326b92aba2d14b1e900519fdafae459f

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08912179B2