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]([NH: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](O)=[O:44])[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.[CH3:70][C:71]1[O:75][N:74]=[C:73]([C:76]2([NH2:79])[CH2:78][CH2:77]2)[N:72]=1>CN(C=O)C>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[O:55][C:35]3=[N:36][C:37]([NH:49][CH2:50][C:51]([F:52])([F:53])[F:54])=[C:38]([C:40]4[CH:48]=[CH:47][CH:46]=[C:42]([C:43](=[O:44])[NH:79][C:76]5([C:73]6[N:72]=[C:71]([CH3:70])[O:75][N:74]=6)[CH2:78][CH2:77]5)[CH:41]=4)[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(NCC(F)(F)F)c(-c3cccc(C(=O)O)c3)cc12
Reactant: Cc1nc(C2(N)CC2)no1
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(NCC(F)(F)F)c(-c3cccc(C(=O)NC4(c5noc(C)n5)CC4)c3)cc12
Temperature: 25 °C
Reaction time: 1 h

Procedure:
2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (23 mg, 0.062 mmol) was added to stirring solution of 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-((2,2,2-trifluoroethyl)amino)furo[2,3-b]pyridin-5-yl)benzoic acid (20 mg, 0.041 mmol), N-ethyl-N-isopropylpropan-2-amine (0.022 mL, 0.12 mmol) and 1-(5-methyl-1,2,4-oxadiazol-3-yl)cyclopropanamine hydrochloride (18 mg, 0.10 mmol) in DMF (1 mL) at rt. The mixture was allowed to stir at rt for 1 h. Then, separately an additional amount of the amine: 1-(5-methyl-1,2,4-oxadiazol-3-yl)cyclopropanamine hydrochloride (18 mg, 0.10 mmol) was taken up in 2 mL of a 1:1 mixture of DMF: N-ethyl-N-isopropylpropan-2-amine and then concentrated. The resulting residue along with additional 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-((2,2,2-trifluoroethyl)amino)furo[2,3-b]pyridin-5-yl)benzoic acid (20 mg, 0.041 mmol), N-ethyl-N-isopropylpropan-2-amine (0.022 mL, 0.12 mmol), and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (23 mg, 0.062 mmol) was added to the original reaction mixture and the mixture was allowed to stir for 1 h at rt. The crude mixture was purified via preparative LC/MS with the following conditions: Column:Waters XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: water with 20-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 20-mM ammonium acetate; Gradient: 30-70% B over 20 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 2.3 mg, and its estimated purity by LCMS analysis was 99%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column:Waters BEH C18, 2.0×50 mm, 1.7-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10 mM ammonium acetate; Temperature: 40° C.; Gradient: 0.5 min hold at 0% B, 0-100% B over 4 minutes, then a 0.5-minute hold at 100% B; Flow: 1 mL/min. retention time: 2.77 min; M+H: 609. Injection 2 conditions: Column:Waters BEH C18, 2.0×50 mm, 1.7-μm particles; Mobile Phase A: 5:95 methanol:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 methanol:water with 10 mM ammonium acetate; Temperature: 40° C.; Gradient: 0.5 min hold at 0% B, 0-100% B over 4 minutes, then a 0.5-minute hold at 100% B; Flow: 0.5 mL/min. retention time: 3.81 min; M+H: 609. Proton NMR was acquired in deuterated DMSO. 1H NMR (500 MHz, DMSO-d6) δ 9.36 (s, 1H), 8.42-8.33 (m, 1H), 8.00-7.90 (m, 4H), 7.70-7.56 (m, 3H), 7.39-7.30 (m, 2H), 6.65-6.58 (m, 1H), 4.25-4.11 (m, 2H), 2.83-2.75 (m, 3H), 2.52 (s, 3H), 1.48-1.42 (m, 2H), 1.37-1.30 (m, 2H).