3-(1-(2,3-Difluorophenyl)-1H-tetrazol-5-yl)-5-((E)-2,5,6,7-tetrahydro-1H-azepin-4-yl)pyridin-2-amine (37 mg, 100 μmol, 1 eq.) was diluted in DCM (1.5 mL). EDC (34.4 mg, 150 μmol, 1.5 eq.), trifluoroacetic acid (17.1 mg, 150 μmol, 1 eq.), and DIEA (53 μL, 300 μmol, 3 eq.) were added. The reaction was stirred at room temperature overnight then concentrated. The product was purified by reversed-phase HPLC purification to give 1-((E)-5-(6-amino-5-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-3,4-dihydro-2H-azepin-1(7H)-yl)-2,2,2-trifluoroethanone (13.6 mg, 30% yield); 1H NMR (300 MHz, DMSO-d6): 8.25 (m, 1H); 7.87 (m, 1H); 7.77 (m, 1H); 7.55 (m, 1H); 7.37 (m, 1H); 5.95-5.7 (m, 1H); 4.12 (m, 2H); 3.75-3.6 (m, 2H); 2.4 (m, 2H); 1.75 (m, 2H).
