Sodium Carbonate → HCID 178419853, Verbindung

A mixture of 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.10 g, 0.49 mmol) and N-(trans-4-(3-chloropyrazin-2-yloxy)cyclohexyl)benzo[d]thiazol-2-amine (0.14 g, 0.39 mmol), prepared as in step 1 of example 9a, in 1,2-dimethoxyethane (2 mL) and aqueous sodium carbonate (2 M, 0.58 mL, 1.16 mmol) was placed under nitrogen atmosphere using 3 evacuation/backfill cycles. Tetrakis triphenylphosphine(palladium) (0.022 g, 0.019 mmol) was added and one more evacuation/backfill cycle was executed. The mixture was then heated to 80° C. After 4 h the mixture was cooled to RT and partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate twice. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give N-(trans-4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)cyclohexyl)benzo[d]thiazol-2-amine (0.13 g, 0.32 mmol, 83% yield). [M+1] 409.2. IC50 (uM): 0.03702.

1. temperatureAfter 4 h the mixture was cooled to RT
2. custompartitioned between ethyl acetate and water
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with ethyl acetate twice
5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting oil was purified by silica gel chromatography

ORD-Eintrag

ord-e1a05b964c6b4c74bd1da79aadef8269

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08952037B2