F[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])[CH:5]=[CH:4][N:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([CH:26]([NH2:28])[CH3:27])[O:23][N:22]=2)=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:25]=[C:24]([CH:26]([NH:28][C:2]3[N:7]=[C:6]([N:8]4[CH2:12][CH2:11][O:10][C:9]4=[O:13])[CH:5]=[CH:4][N:3]=3)[CH3:27])[O:23][N:22]=2)=[CH:19][CH:20]=1A solution of 3-(2-fluoropyrimidin-4-yl)oxazolidin-2-one (89.1 mg, 0.487 mmol), 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethanamine (115.9 mg, 0.518 mmol, 1.06 equiv), and DIPEA (0.20 mL, 1.1 mmol, 2.4 equiv) in DMSO (1.5 mL) was heated at 110° C. for 100 min. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (MeOH in CH2Cl2 0 to 5%) provided 3-(2-(1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one (18.2 mg, white solid) in 10.3% yield.
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