1-Methylimidazole → 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl)benzamide

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Reaction Steps

To a mixture of 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (40 mg, 0.1 mmol) and 3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one hydrochloride (22 mg, 0.1 mmol) in 3 mL of DCM was added EDCI (58 mg, 0.3 mmol) followed by N-methylimidazole (25 mg, 0.3 mmol). The mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with EtOAc to give 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl)benzamide (15 mg, 26%) as white solid. 1H NMR (300 MHz, DMSO): δ 10.82 (s, 1H), 10.22 (s, 1H), 9.43 (s, 1H), 8.98 (s, 1H), 8.64 (d, 1H, J=8.1 Hz), 8.12-8.02 (m, 3H), 7.87-7.54 (m, 5H), 7.01 (d, 1H, J=9.0 Hz), 3.82 (s, 3H), 3.76 (s, 3H). LC-MS: 568 [M+H]+, tR=1.54 min. HPLC: 97.16% at 214 nm, 96.94% at 254 nm, tR=2.86 min.

Provenance & Evidence