Reaction SMILES: [CH2:1](N(C(C)C)C(C)C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:40][C:20]3=[N:21][C:22]([CH2:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[C:23]([C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)[C:28](O)=[O:29])[CH:24]=[C:19]3[C:18]=2[C:41](=[O:44])[NH:42][CH3:43])=[CH:13][CH:12]=1.CN(C([O:52][N:53]1N=[N:60][C:55]2[CH:56]=[CH:57][CH:58]=[N:59][C:54]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O1C=NC(CN)=N1>CN(C=O)C.CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:40][C:20]3=[N:21][C:22]([CH2:34][CH2:35][C:36]([F:39])([F:37])[F:38])=[C:23]([C:25]4[CH:33]=[CH:32][CH:31]=[C:27]([C:28](=[O:29])[NH:60][C:55]([C:54]5[N:59]=[C:58]([CH3:57])[O:52][N:53]=5)([CH3:56])[CH3:1])[CH:26]=4)[CH:24]=[C:19]3[C:18]=2[C:41]([NH:42][CH3:43])=[O:44])=[CH:13][CH:12]=1
Reactant: CNC(=O)c1c(-c2ccc(F)cc2)oc2nc(CCC(F)(F)F)c(-c3cccc(C(=O)O)c3)cc12
Reactant: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Reactant: CCN(C(C)C)C(C)C
Agent: F[P-](F)(F)(F)(F)F
Agent: NCc1ncon1
Solvent: CN(C)C=O
Solvent: CO
Product: CNC(=O)c1c(-c2ccc(F)cc2)oc2nc(CCC(F)(F)F)c(-c3cccc(C(=O)NC(C)(C)c4noc(C)n4)c3)cc12
Temperature: 25 °C
Reaction time: 1 h

Procedure:
N-ethyl-N-isopropylpropan-2-amine (0.043 mL, 0.25 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 (15 mg, 0.031 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (18 mg, 0.046 mmol) and 1,2,4-Oxadiazole-3-methanamine, α,α,5-trimethyl hydrochloride (5.5 mg, 0.031 mmol) in DMF (1 mL) at rt. The mixture was allowed to stir at rt for 1 h. LCMS shows complete reaction. The solution was diluted with MeOH, filtered and purified via preparative LC/MS with the following conditions: Column:Waters XBridge C18, 19×200 mm, 5-μm particles; Guard Column:Waters XBridge C18, 19×10 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: 20-80% B over 20 minutes, then a 5-minute hold at100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 2.4 mg, and its estimated purity by LCMS analysis was 100%. 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. 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. Proton NMR was acquired in deuterated DMSO. LC-MS retention time: 1.86 min; m/z (MH+): 610. 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 8.68 (br s, 1H), 8.50 (br s, 1H), 8.05 (br s, 2H), 8.00-7.86 (m, 3H), 7.61 (d, J=11.0 Hz, 2H), 7.41 (t, J=8.4 Hz, 2H), 3.03-2.97 (m, 2H), 3.22.81 (s, 3H), 2.79-2.71 (m, 2H), 2.53 (s, 3H), 1.67 (s, 6H).