Reaction SMILES: CCN(C(C)C)C(C)C.Cl.Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1([NH2:21])[CH2:20][CH2:19]1.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=1[C:32]1[CH:33]=[C:34]2[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=3)[O:38][C:35]2=[N:36][CH:37]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](=[O:28])[NH:21][C:18]2([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)[CH2:20][CH2:19]2)=[CH:25][C:24]=1[C:32]1[CH:33]=[C:34]2[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]([C:45]3[CH:46]=[CH:47][C:48]([F:51])=[CH:49][CH:50]=3)[O:38][C:35]2=[N:36][CH:37]=1
Reactant: NC1(c2ccccn2)CC1
Reactant: COC(=O)c1c(-c2ccc(F)cc2)oc2ncc(-c3cc(C(=O)O)ccc3Cl)cc12
Agent: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: Cl
Agent: F[P-](F)(F)(F)(F)F
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Solvent: CCN(C(C)C)C(C)C
Product: COC(=O)c1c(-c2ccc(F)cc2)oc2ncc(-c3cc(C(=O)NC4(c5ccccn5)CC4)ccc3Cl)cc12
Reaction time: 1 h

Procedure:
DIEA (142 μL, 0.810 mmol) was added to a stirring solution of 1-(pyridin-2-yl)cyclopropanamine dihydrochloride (84 mg, 0.405 mmol), 4-chloro-3-(2-(4-fluorophenyl)-3-(methoxycarbonyl)furo[2,3-b]pyridin-5-yl)benzoic acid (115 mg, 0.270 mmol) and HATU (154 mg, 0.405 mmol) in DMF (2.7 mL) at room temperature. It was allowed to stir for 1 hour. The mixture was diluted with ethyl acetate and washed with sat NaHCO3, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give crude methyl 5-(2-chloro-5-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylate. The crude residue was diluted with MeOH (4 mL) and treated with NaOH (810 μL, 0.810 mmol) in H2O; the reaction was heated to 60° C. and allowed to stir for 1 hr. The mixture was diluted with EtOAc and washed with 1M HCl, and sat NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to give crude 5-(2-chloro-5-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)-2-(4-fluorophenyl)furo[2,3-b]pyridine-3-carboxylic acid. The crude residue was diluted with DMF (2 mL) and treated with HATU (154 mg, 0.405 mmol), methanamine (675 μL, 1.35 mmol, 2 M in THF) in THF, followed by DIEA (142 μL, 0.810 mmol). The reaction was allowed to stir at room temperature for 1 hour. The mixture was concentrated and purified on silica gel (Biotage, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the expected product consistent by LCMS and NMR. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.40 (1H, s), 8.52 (1H, d, J=4.77 Hz), 8.50 (1H, d, J=2.01 Hz), 8.44 (1H, d, J=4.77 Hz), 8.23 (1H, d, J=2.01 Hz), 8.12 (1H, d, J=2.01 Hz), 7.97-8.09 (3H, m), 7.78 (1H, d, J=8.28 Hz), 7.67 (1H, td, J=7.72, 1.88 Hz), 7.39-7.47 (2H, m), 7.36 (1H, d, J=8.03 Hz), 7.15 (1H, dd, J=7.40, 4.89 Hz), 2.83 (3H, d, J=4.52 Hz), 1.50-1.60 (2H, m), 1.22-1.32 (2H, m). LC-MS retention time: 1.31 min; m/z (MH+): 541. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5u 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 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% MeOH/95% H2O/10 mM ammonium bicarbonate, Solvent B=95% MeOH/5% H2O/10 mM ammonium bicarbonate, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Phenomenex Gemini C1-C-18, 4.6×150 mm, 3 mm, Rt=9.66 min, purity=98%; Column. Waters Xbridge Phenyl column 4 6×150 mm, 3.5 mm, Rt=9.69 min, purity=98%.