BUTTPARK 80\07-61

To a solution of To a dry reaction vial under nitrogen was added (S)-2-((fer?- butoxycarbonyl)amino)-3-(3, 5-difluorophenyl)propanoic acid (45 mg, 0.149 mmol), 2- amino-4-fluoro-3-methylbenzoic acid (25.2 mg, 0.149 mmol) and anhydrous Pyridine (0.9 mL). The reaction was flushed with argon, treated with diphenyl phosphite (125 , (1645) 0.646 mmol) and heated at 75 C for 80 min. The reaction was treated with N-(7-amino-4- chloro-1 -methyl- lH-indazol-3-yl)-N-(4-methoxybenzyl)methanesulfonamide (Int 17d, 59 mg, 0.149 mmol) and heated at 75 C for 18 h. The solvent was removed under a gentle stream of nitrogen and the crude matenal was purified via silica gel chromatography (80 g SiC column, 0-100% ethyl acetate :hexanes) to afford the title compound, 120 mg. (1646) LC/MS m/z = 755.3 (M-55); 833.3 (M+Na). Column: Waters Aquity UPLC BEH CI 8, 2.1 mm x 50 mm, 1.7 mupiiota particles; Mobile Phase A: 100% water with 0.05% TFA; (1647) Mobile Phase B: 100% acetonitnle with 0.05% TFA; Temperature: 40 C; Gradient: 2 %B to 98 %B over 1.5 min, then a 1.5 min hold at 100 %B; Flow: 0.8 mL/min; Detection: UV (220 nm); Retention Time: 1.94 min.First Step Step 1: Methyl 2-amino-4-fluoro-3-methylbenzoateA solution (1.0 M) of

Molecular Weight:169.15
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:169.05390666
Monoisotopic Mass:169.05390666
Topological Polar Surface Area:63.3
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes