Diisopropylethylamine → HCID 131733534, compound

Temperature

45 °C

To 2-amino-6-ethynylpyridine (G55, 203 mg) synthesized according to the method described in WO2012/052451 A1, N-Boc-N-methyl-L-alanine (524 mg), and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.31 g), N,N-diisopropylethylamine (1.2 mL) and N,N-dimethylformamide (4.5 mL) were added at room temperature, and the mixture was stirred at 45° C. for 12 hours. The reaction mixture was cooled on ice, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl (1-((6-ethynylpyridin-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (G56, 180 mg) as white solid.

1. additionwere added at room temperature
2. temperatureThe reaction mixture was cooled on ice
3. customThe organic layer was separated
4. washwashed successively with water and saturated aqueous sodium chloride
5. dry with materialdried over anhydrous sodium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography

ORD record

ord-55911c60e7a1495b9dca71e368b7e645

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145415B2