NC1C=CC(CC(O)=O)=CC=1.C1C(=O)N(Br)C(=O)C1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([OH:30])=O)=[CH:23][C:22]=1[Br:31].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:53][N:54]([CH3:58])[CH2:55][CH2:56][NH2:57].CCN(CC)CC>CC#N.CC(O)=O.C(Cl)Cl>[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:57][CH2:56][CH2:55][N:54]([CH3:58])[CH3:53])=[O:30])=[CH:23][C:22]=1[Br:31]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 N′,N′-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).
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