Reaction SMILES: [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:31][C:11]3=[N:12][C:13]([CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:14]([C:16]4[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=4)[C:19](O)=[O:20])[CH:15]=[C:10]3[C:9]=2[C:32](=[O:35])[NH:33][CH3:34])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.CN([C:48]([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>CN(C=O)C>[O:52]1[CH:48]=[N:59][C:54]([C:55]2([NH:60][C:19]([C:18]3[CH:17]=[C:16]([C:14]4[CH:15]=[C:10]5[C:9]([C:32]([NH:33][CH3:34])=[O:35])=[C:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)[O:31][C:11]5=[N:12][C:13]=4[CH2:25][CH2:26][C:27]([F:29])([F:30])[F:28])[CH:24]=[CH:23][CH:22]=3)=[O:20])[CH2:56][CH2:57][CH2:58]2)=[N:53]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
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)NC4(c5ncon5)CCC4)c3)cc12
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
N-(1-(1,2,4-oxadiazol-3-yl)cyclobutyl)-2-methylpropane-2-sulfinamide (45 mg, 0.19 mmol) was taken up in 1 mL of MeOH and treated with 1 mL of HCl (2M in Et2O) at rt and allowed to stir for 30 min at rt. The reaction was then concentrated to dryness azeotroping with toluene 3× to give 1-(1,2,4-oxadiazol-3-yl)cyclobutanamine hydrochloride (32 mg, 0.18 mmol). Then 14 mg (0.077 mmol) of this material was combined with 3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(3,3,3-trifluoropropyl)furo[2,3-b]pyridin-5-yl)benzoic acid (25 mg, 0.051 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.027 mL, 0.15 mmol) in DMF (1 mL) at rt. To this stirring solution 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (29 mg, 0.077 mmol) was added. The mixture was allowed to stir at rt for 30 min. The crude reaction 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: 40-80% 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 20.2 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. retention time: 3.02 min; M+H: 608. 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; MobilePhase 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: 4.06 min; M+H: 608. Proton NMR was acquired in deuterated DMSO. 1H NMR (500 MHz, DMSO-d6) δ 9.48 (s, 1H), 9.33 (s, 1H), 8.55-8.46 (m, 1H), 8.10-8.02 (m, 2H), 7.98 (s, 3H), 7.69-7.59 (m, 2H), 7.46-7.37 (m, 2H), 3.05-2.97 (m, 2H), 2.85-2.71 (m, 5H), 2.67-2.56 (m, 4H), 2.10-1.99 (m, 2H).