1-Methylimidazole → Methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-methoxybenzoate

Participants

Reaction Steps

To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (110 mg, 0.27 mmol) and methyl 4-amino-2-methoxybenzoate (48 mg, 0.27 mmol) in dichloromethane (15 mL) were added the solution of 1-methyl-1H-imidazole (87 mg, 1.1 mmol) and EDCI (203 mg, 1.1 mmol) in dichloromethane (5 mL), the reaction mixture was stirred at room temperature for 15 hours, the solvent was removed in vacuo, then methanol (5 mL) was added, the precipitate was collected by filtration and washed with methanol (5 mL) to afford methyl 4-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxamido)-2-methoxybenzoate (126 mg, 80.8%) as an orange solid. LC-MS: 579 [M+H]+, tR=1.58 min.

Provenance & Evidence