Hydrochloric Acid → HCID 90100317, compound

Temperature

-78 °C

100 mg (0.28 mmol) of tert-butyl((4-fluorophenyl)sulfonyl)(thiazol-2-yl)carbamate was dissolved in 5 mL of tetrahydrofuran under nitrogen gas, and cooled to −78° C. After adding 0.26 mL (0.42 mmol) of n-butyllithium (1.6 M in tetrahydrofuran) slowly, the mixture was stirred for 30 minutes as maintaining −78° C. 23 mg (0.13 mmol) of 2-(furan-3-yl)nicotinaldehyde was dissolved in 0.5 mL of tetrahydrofuran, and added to the above reacting solution. As warming from −78° C. to room temperature, the reacting solution was stirred for 24 hours. Ethyl acetate and water/1 N-hydrochloride were added to the reacting solution, and it was stirred. After separating layers, the organic layer only was collected and concentrated under reduced pressure. The obtained residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=1:1) to obtain 6 mg (5.2% yield) of the title compound.

1. temperatureas maintaining −78° C
2. additionadded to the
3. temperatureAs warming from −78° C. to room temperature
4. stirringthe reacting solution was stirred for 24 hours
5. stirringwas stirred
6. customAfter separating layers
7. customthe organic layer only was collected
8. concentrationconcentrated under reduced pressure
9. customThe obtained residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=1:1)

ORD record

ord-c0da594b32764e7aa34e8349de3cb206

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376429B2