Triethylamine → HCID 86666738, compound

1,1-dimethylethyl hydrazinecarboxylate (2.59 g, 19.58 mmol) and triethylamine (2.98 mL, 21.36 mmol) were dissolved in Dichloromethane (DCM) (50 mL). 5-chloro-2-pyrazinecarbonyl chloride (I47) (3.15 g, 17.80 mmol) dissolved in Dichloromethane (DCM) (50 mL) was added dropwise at 0° C. and the mixture allowed to reach room temperature over 16 hr. Solvents were removed in vacuo and the residue was partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (50 mL). The aqueous phase was extracted with ethyl acetate (3×100 mL), combined extracts were washed with brine (100 mL) dried over anhydrous sodium sulfate and concentrated to a crude solid (5.05 g). The product was purified by flash chromatography (Isolera, 100 g, 0-100% Methanol:Dichloromethane (1:9)/Dichloromethane) to afford product in 4.63 g.

1. additionwas added dropwise at 0° C.
2. customSolvents were removed in vacuo
3. customthe residue was partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (50 mL)
4. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
5. washwere washed with brine (100 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated to a crude solid (5.05 g)
8. customThe product was purified by flash chromatography (Isolera, 100 g, 0-100% Methanol:Dichloromethane (1:9)/Dichloromethane)
9. customto afford product in 4.63 g

ORD record

ord-767ba3c620c840febc4426b743a95625

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2