[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[F:24][C@H:25]1[CH2:27][C@@H:26]1[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:40])=[C:37]([CH:39]=2)[NH2:38])[N:29]=1>ClCCl.N1C=CC=CC=1>[F:24][C@H:25]1[CH2:27][C@@H:26]1[C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:40])=[C:37]([NH:38][C:10]([C:3]3[N:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[N:1][CH:2]=3)=[O:12])[CH:39]=2)[N:29]=1To a stirring suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (52 mg, 0.32 mmol) in anhydrous dichloromethane (2 mL) at 0° C. under Argon was added dropwise oxalyl chloride (56 μL, 0.64 mmol). Then, a drop of anhydrous DMF was added and the reaction mixture was stirred at room temperature for 1.5 hours. The solvent was concentrated and the crude solid was added portion-wise to a stirring solution of 5-(5-((1R,2S)-2-fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (131) (62 mg, 0.27 mmol) in anhydrous pyridine (1 mL) at 0° C. The reaction was stirred at room temperature under Argon for 30 minutes and quenched with water. The crude product was purified by preparative HPLC to yield N-(5-(5-((1R,2S)-2-fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F110). MS m/z 378.1 (M+1)+.
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