Nitrogen → HCID 59784467, compound

To a solution of 2-(4-amino-3-methyl-5-nitro-phenyl)-2,2-difluoro-1-morpholin-4-yl-ethanone (945 mg, 3 mmol) in anhydrous THF (15 mL) was added BH3.S(CH3)2 (1 mL, 790 mg, 10.4 mmol) dropwise and slowly under N2 at 0° C. The mixture was stirred under N2 at the room temperature for 19 h and then refluxed under N2 for 1.5 h. After being cooled to 0° C., MeOH (2 mL) was added dropwise and slowly. The reaction mixture was poured into 20% aqueous NaHCO3 solution (150 mL) and extracted with EtOAc (3×50 mL). The organic extract was washed with brine (2×10 mL), dried over Na2SO4 and concentrated. The residue was purified by chromatography (2:3 hexanes/EtOAc) to afford the title compound (740 mg, 82%). 1H NMR (CDCl3) δ 2.29 (s, 3H), 2.56-2.61 (4H), 2.93 (t, J=12 Hz, 2H, CH2CF2), 3.62-3.63 (4H), 6.34 (br s, 2H NH), 7.44 (s, 1H), 8.25 (s, 1H). (s, 1H). ESI-MS m/z 302 (MH+).

1. customat 0° C
2. temperaturerefluxed under N2 for 1.5 h
3. temperatureAfter being cooled to 0° C.
4. extractionextracted with EtOAc (3×50 mL)
5. extractionThe organic extract
6. washwas washed with brine (2×10 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe residue was purified by chromatography (2:3 hexanes/EtOAc)

ORD record

ord-180eeed965aa4a3988b777f2d5123e95

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629147B2