Methanol → HCID 68411189, compound

To a solution of 1-(2-chlorophenyl)-5-[(5-methylpyridin-2-yl)thio]-1H-pyrazole-3-carbaldehyde (422 mg) in tetrahydrofuran (4 mL) were added 40% methylamine-methanol solution (1.3 mL) and methanol (4 mL) at 0° C. The mixture was stirred at room temperature for 16 hr, and concentrated under reduced pressure. The residue was dissolved in methanol (4 mL), sodium borohydride (60 mg) was added at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 433 mg, 98%).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in methanol (4 mL)
3. additionsodium borohydride (60 mg) was added at 0° C.
4. stirringthe mixture was stirred at room temperature for 1 hr
5. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
6. additionwas added to the residue
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-b5eaedc73860421fa05816b0b2b4b8a3

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334301B2