Triethylamine → HCID 58994585, compound

To a solution of (4-amino-phenyl)-acetic acid (320 mg, 2.10 mmol) in CH3CN (4 mL) and AcOH (2 mL) at 0° C. was added NBS (373 mg, 2.10 mmol) in CH3CN (3 mL). The reaction was allowed to warm to room temperature over 1 h and then concentrated in vacuo to give a mixture of (4-amino-3-bromo-phenyl)-acetic acid and starting material which was used without further purification. The crude (4-amino-3-bromo-phenyl)-acetic acid (490 mg, 2.12 mmol), EDCI (487 mg, 2.54 mmol), HOBt (343 mg, 2.54 mmol), and N1,N1-dimethyl-ethane-1,2-diamine (281 mg, 3.19 mmol) were slurried in DCM (10 mL), treated with NEt3 (910 μL, 6.36 mmol) and stirred overnight. The reaction was diluted with DCM (50 mL), washed with water (2×50 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by preparative TLC (10% MeOH—CHCl3) to afford 70 mg (11%) of the title compound. 1H-NMR (CDCl3; 400 MHz) δ 7.25 (s, 1H, J=2.0 Hz), 6.93 (dd, 1H, J=8.1, 2.0 Hz), 6.65 (d, 1H, J=8.1 Hz), 6.04 (br s, 1H), 4.03 (br s, 2H), 3.32 (s, 2H), 3.24-3.19 (m, 2H), 2.30-2.27 (m, 2H), 2.11 (s, 6H).

1. concentrationconcentrated in vacuo
2. customto give
3. customwas used without further purification
4. washwashed with water (2×50 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by preparative TLC (10% MeOH—CHCl3)

ORD record

ord-bc16bdd8435446428ff295813fa0cf4d

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674100B2