Monomethylamine methanol → HCID 68410819, compound

N-(3-Formyl-1-phenyl-1H-pyrazol-5-yl)benzamide (303 mg) was dissolved in tetrahydrofuran (5 mL) and methanol (3 mL), and 40% methylamine-methanol solution (1.1 mL) was added at room temperature. After stirring for 18 hr, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (3 mL), sodium borohydride (118 mg) was added under ice-cooling and the mixture was further stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→ethyl acetate) to give a free base of the title compound as a pale-yellow amorphous form (yield 248 mg). The obtained free base was dissolved in tetrahydrofuran (5 mL), and the mixture was added to a solution of fumaric acid (94 mg) in ethanol (10 mL). The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to give the title compound as colorless crystals (yield 137 mg, yield 37%).

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in methanol (3 mL)
3. additionsodium borohydride (118 mg) was added under ice-
4. temperaturecooling
5. stirringthe mixture was further stirred at room temperature for 1 hr
6. customThe solvent was evaporated under reduced pressure, water
7. additionwas added to the residue
8. extractionthe mixture was extracted with ethyl acetate
9. washThe extract was washed with saturated brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→ethyl acetate)

ORD record

ord-9927bd11bd1046679d327531afe83d64

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334301B2