1-Methylimidazole → 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide

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Reaction Steps

The mixture of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylic acid (50 mg, 0.12 mmol), 2-(pyridin-4-yl)ethanamine (22 mg, 0.18 mmol), EDCI (69 mg, 0.36 mmol) and 1-methyl-1H-imidazole (50 mg, 0.60 mmol) in 25 mL of DCM was stirred at room temperature for 16 hours. Excess of DCM was removed under reduced pressure and the residue was washed with H2O (30 mL) and EtOAc (20 mL) dried under reduced pressure to give 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)piperidine-4-carboxamide (30 mg, 48%) as a yellow solid. 1H NMR (300 MHz, CD3OD): δ 8.62 (s, 1H), 8.44-8.42 (m, 2H), 7.61 (d, 1H, J=2.4 Hz), 7.31-7.18 (m, 3H), 6.95 (d, 1H, J=8.7 Hz), 4.82-4.77 (m, 2H), 3.86 (s, 3H), 3.84 (s, 3H), 3.47 (t, 2H, J=6.9 Hz), 2.95-2.92 (m, 2H), 2.86 (t, 2H, J=6.9 Hz), 2.44 (brs, 1H), 1.74-1.62 (m, 4H). LC-MS: 520 [M+H]+, 260 [M/2+H]+, 518 [M−H]−, tR=1.29 min. HPLC: 97.06% at 214 nm, 97.32% at 254 nm, tR=3.47 min.

Provenance & Evidence