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

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Reaction Steps

A mixture of 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (100 mg, 0.245 mmol), 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol (53 mg, 0.27 mmol), EDCI (94 mg, 0.49 mmol) and DMAP (90 mg, 0.735 mmol) in 5 mL of DMF was stirred at room temperature for 40 hours. The mixture was poured into water and extracted with EtOAc (3×10 mL). The water layer was allowed to stand overnight then filtered to give 3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl)benzamide (28 mg, 19.5%) as white solid. 1H NMR (300 MHz, DMSO): δ 10.67 (s, 1H), 10.20 (s, 1H), 9.41 (s, 1H), 8.96 (s, 1H), 9.61 (d, 1H, J=7.8 Hz), 8.10 (d, 1H, J=8.1 Hz), 7.96-7.93 (m, 3H), 7.83-7.68 (m, 4H), 7.55 (d, 1H, J=6.6 Hz), 6.99 (d, 1H, J=9.0 Hz), 3.81 (s, 3H), 3.74 (s, 3H). LC-MS: 584 [M+H]+, 582 [M−H]−, tR=1.61 min. HPLC: 96.43% at 214 nm, 96.83% at 254 nm, tR=4.60 min.

Provenance & Evidence