Aniline → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(1-phenyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Participants

Reaction Steps

Aniline (18.9 mg, 0.203 mmol) in ACN (2 mL) was cooled to 0° C., t-Butyl nitrite (31.4 mg, 0.305 mmol) was added dropwise, the reaction stirred for 5 minutes, then trimethylsilylazide (50.7 mg, 0.244 mmol) was added in one portion and the mixture allowed to warm to rt and stirred for hours. Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (100 mg, 0.203 mmol) and sodium ascorbate (8.1 mg, 0.040 mmol) were added, followed by copper sulphate (1.6 mg, 0.010 mmol) in 0.1 mL of water. The reaction was stirred at rt for 18 hours, filtered through a pad of keiselguhr and the solvent removed under vacuum to yield a brown gum. The crude material was purified by preperative HPLC to give the product as an off white solid 28 mg, 22.6% yield.

Provenance & Evidence