Reaction SMILES: CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:55][C:35]3=[N:36][C:37]([CH2:49][CH2:50][C:51]([F:54])([F:53])[F:52])=[C:38]([C:40]4[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=4)[C:43]([OH:45])=O)[CH:39]=[C:34]3[C:33]=2[C:56](=[O:59])[NH:57][CH3:58])=[CH:28][CH:27]=1.C(N(C(C)C)C(C)C)C.Cl.[O:70]1[CH:74]=[N:73][C:72]([C:75]([NH2:78])([CH3:77])[CH3:76])=[N:71]1>CN(C=O)C>[O:70]1[CH:74]=[N:73][C:72]([C:75]([NH:78][C:43]([C:42]2[CH:41]=[C:40]([C:38]3[CH:39]=[C:34]4[C:33]([C:56]([NH:57][CH3:58])=[O:59])=[C:32]([C:29]5[CH:28]=[CH:27][C:26]([F:25])=[CH:31][CH:30]=5)[O:55][C:35]4=[N:36][C:37]=3[CH2:49][CH2:50][C:51]([F:53])([F:52])[F:54])[CH:48]=[CH:47][CH:46]=2)=[O:45])([CH3:77])[CH3:76])=[N:71]1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[O:55][C:35]3=[N:36][C:37]([CH2:49][CH2:50][C:51]([F:53])([F:52])[F:54])=[CH:38][CH:39]=[C:34]3[C:33]=2[C:56]([NH:57][CH3:58])=[O:59])=[CH:30][CH:31]=1
Reactant: CNC(=O)c1c(-c2ccc(F)cc2)oc2nc(CCC(F)(F)F)c(-c3cccc(C(=O)O)c3)cc12
Reactant: CC(C)(N)c1ncon1
Agent: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: Cl
Agent: F[P-](F)(F)(F)(F)F
Solvent: CCN(C(C)C)C(C)C
Solvent: CN(C)C=O
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2nc(CCC(F)(F)F)c(-c3cccc(C(=O)NC(C)(C)c4ncon4)c3)cc12
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2nc(CCC(F)(F)F)ccc12
Temperature: 25 °C
Reaction time: 1 h
Yield: 151.9 %

Procedure:
2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (879 mg, 2.31 mmol) was added to stirring solution of 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridin-5-yl)benzoic acid (750 mg, 1.54 mmol), N-ethyl-N-isopropylpropan-2-amine (0.81 ml, 4.6 mmol) and 2-(1,2,4-oxadiazol-3-yl)propan-2-amine hydrochloride (277 mg, 1.70 mmol) in DMF (10 ml) at rt. The mixture was allowed to stir at rt for 1 h. The reaction mixture was then concentrated and purified on silica gel (Biotage, EtOAc/DCM gradient, fraction collection at λ=254 nm) to give the expected product 5-(3-(2-(1,2,4-oxadiazol-3-yl)propan-2-yl)carbamoyl)phenyl)-2-(4-fluorophenyl)-N-methyl-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridine-3-carboxamide (711 mg, 1.17 mmol, 76% yield) consistent by LCMS and NMR. LC-MS retention time: 1.76 min; m/z (MH+): 596. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 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 1 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 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. 1H NMR (500 MHz, DMSO-d6) δ 9.43 (s, 1H), 8.77 (s, 1H), 8.51 (q, J=4.3 Hz, 1H), 8.11-8.03 (m, 1H), 7.98 (s, 1H), 7.93 (d, J=7.6 Hz, 1H), 7.90 (s, 1H), 7.70 (m, 1H), 7.62 (m, 1H), 7.41 (t, J=8.8 Hz, 2H), 3.04 (m, 2H), 2.82 (d, J=4.4 Hz, 3H), 2.75 (m, 2H), 1.71 (s, 6H); 13C NMR (126 MHz, DMSO-d6) δ 173.9, 166.4, 165.7, 162.4, 163.0 (d, J=247.5 Hz), 158.7, 151.9, 151.3, 138.7, 134.7, 133.0, 132.2, 131.6, 129.9 (d, J=8.2 Hz), 128.4, 127.1, 127.4 (q, J=275.0 Hz), 125.2, 117.5, 116.0 (d, J=22.5 Hz), 112.6, 51.1, 31.4 (q, J=27.5 Hz), 27.2, 26.6, 26.2; 19F NMR (470 MHz, DMSO-d6) δ 64.8, −109.9 HRMS (+ESI)(MH+) Calcd for C30H26F4N5O4: 596.1915. Found 596.1901; IR (KBr powder) 3600-2800, 1650-1638, 1510 cm−1. Anal Calcd. (%) for C30H25F4N5O4: C, 60.50; H, 4.23; N, 11.76. Found: C, 60.61; H, 4.01; N, 11.56.