Morpholine → HCID 81523617, compound

2-Bromo-5-(trifluoromethyl)benzoic acid (200 mg, 0.74 mmol) was dissolved in DMF (4.65 mL) and HATU (424 mg, 1.12 mmol) added to the resultant mixture at rt. The solution was stirred for 10 min then treated with N,N-diisopropylethylamine (0.51 mL, 3.0 mmol) and morpholine (0.096 mL, 1.1 mmol). The reaction was stirred for 15 hours then quenched by the addition of saturated NH4Cl (5 mL) and EtOAc (5 mL). The aqueous phase was extracted with ethyl acetate (3×10 mL) and the combined organic extracts washed with brine, dried over Na2SO4 and concentrated to dryness. The crude product was purified by FCC to give the title compound. 1H NMR (500 MHz, CDCl3) δ 7.76-7.71 (m, 1H), 7.55-7.49 (m, 2H), 3.92-3.86 (m, 1H), 3.83-3.69 (m, 4H), 3.66-3.58 (m, 1H), 3.32-3.24 (m, 1H), 3.25-3.17 (m, 1H).

1. stirringThe reaction was stirred for 15 hours
2. customthen quenched by the addition of saturated NH4Cl (5 mL) and EtOAc (5 mL)
3. extractionThe aqueous phase was extracted with ethyl acetate (3×10 mL)
4. washthe combined organic extracts washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated to dryness
7. customThe crude product was purified by FCC

ORD record

ord-4def60b8cd764d5bbf66c0f29a640ed0

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079866B2