Cyclobutylamine → HCID 89782174, compound

Temperature

23 °C

Propylphosphonic anhydride solution (T3P; Alfa Aesar, Ward Hill, Mass.; ≧50 wt % in EtOAc; 6.06 mL, 10.18 mmol) was added (dropwise, over 1 min) to a suspension of 2-amino-3-bromobenzoic acid (Aldrich; 2.00 g, 9.26 mmol) and cyclobutylamine (Aldrich; 2.37 mL, 27.8 mmol) in EtOAc (20 mL) at 0° C. The resulting solution was warmed to 23° C. and stirred for 1.5 h Additional propylphosphonic anhydride solution (≧50 wt % in EtOAc; 1.21 mL, 2.04 mmol) and cyclobutylamine (0.790 mL, 9.27 mmol) were sequentially added, and the resulting mixture was stirred at 23° C. for 3 h. The reaction mixture was then partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated, sequentially washed with saturated aqueous NaHCO3 (2×50 mL), and brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give 2-amino-3-bromo-N-cyclobutylbenzamide (2.127 g, 7.90 mmol, 85% yield) as a light-yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.50 (1H, dd, J=7.8, 1.2 Hz), 7.27 (1H, d, J=7.8 Hz), 6.52 (1H, t, J=7.8 Hz), 6.12 (2H, br. s.), 5.81-6.06 (1H, m), 4.53 (1H, sxt, J=8.0 Hz), 2.35-2.53 (2H, m), 1.90-1.98 (2H, m), 1.74-1.82 (2H, m). m/z (ESI, +ve) 268.9/271.0 (M+H)+.

1. additionwere sequentially added
2. customThe reaction mixture was then partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (100 mL)
3. customThe organic layer was separated
4. washsequentially washed with saturated aqueous NaHCO3 (2×50 mL), and brine (50 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-077aec6c0cb64a3295ccf06d0a724c59

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394297B2