Reaction SMILES: [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28](=[O:39])[NH:29][C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)([CH3:32])[CH3:31])[CH:23]=4)=[C:18]([N+:40]([O-:42])=[O:41])[C:11]=3[C:12]=2[C:13]([O:15]CC)=O)=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)CCl.FC1C=CC(C2OC3C=CC(C4C=CC=C([C:74](=O)[NH:75]C(C5C=CC=CC=5)(C)C)C=4)=C([N+]([O-])=O)C=3C=2C(O)=O)=CC=1.CN.ON1C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CCO.CCOC(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28](=[O:39])[NH:29][C:30]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)([CH3:32])[CH3:31])[CH:23]=4)=[C:18]([N+:40]([O-:42])=[O:41])[C:11]=3[C:12]=2[C:13]([NH:75][CH3:74])=[O:15])=[CH:4][CH:3]=1
Reactant: CC(C)(NC(=O)c1cccc(-c2ccc3oc(-c4ccc(F)cc4)c(C(=O)O)c3c2[N+](=O)[O-])c1)c1ccccc1
Reactant: CCOC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cccc(C(=O)NC(C)(C)c4ccccc4)c3)c([N+](=O)[O-])c12
Agent: CN
Agent: On1nnc2cccnc21
Agent: [Na+]
Solvent: CCO
Solvent: CCOC(C)=O
Solvent: ClCCl
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2ccc(-c3cccc(C(=O)NC(C)(C)c4ccccc4)c3)c([N+](=O)[O-])c12
Temperature: 60 °C
Reaction time: 8 h
Yield: 75.4 %

Procedure:
Step 1: ethyl 2-(4-fluorophenyl)-4-nitro-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxylate (300 mg, 0.529 mmol) was diluted with EtOH (10 mL) and treated with NaOH (2.1 mL, 2.12 mmol, 1N aq.) and the mixture, which became a slurry, was allowed to stir overnight at 60° C. The reaction was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated. Step 2: EDC (128 mg, 0.668 mmol) was added to a stirring solution of the crude 2-(4-fluorophenyl)-4-nitro-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxylic acid (300 mg, 0.557 mmol), methanamine (306 μL, 0.613 mmol), 1-hydroxy-7-azabenzotriazole (83 mg, 0.613 mmol), DIEA (204 μL, 1.170 mmol) in DCM (5.5 mL) at rt. It was allowed to stir for 3 days. The slurry had gone into solution over that period of time. The mixture was concentrated and purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the titled compound (220 mg, 95%). 1H NMR (500 MHz, CD3OD) δ ppm 7.90-7.99 (3 H, m), 7.85-7.90 (1 H, m), 7.82-7.84 (1 H, m), 7.49-7.56 (3 H, m), 7.45 (2H, d, J=7.32 Hz), 7.27-7.34 (4 H, m), 7.19 (1 H, t, J=7.32 Hz), 2.87 (3 H, s), 1.76 (6H, s). LC-MS retention time: 1.62 min; m/z (MH+): 552. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% CH3CN/95% H2O/0.1% TFA, Solvent B=95% CH3CN/5% H2O/0.1% TFA, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Waters Sunfire C-18, 4.6×150 mm, 3.5 μm, Rt=13.60 min, purity=94%; Column: Waters Xbridge Phenyl column 4 6×150 mm, 3.5 μm, Rt=12.66 min, purity=96%.