Diisopropylethylamine → N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-[5-(4-methoxyphenyl)pyrimidin-2-ylamino]acetamide HCl salt

Participants

Reaction Steps

Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14 mg, 0.08 mmol, 1.5 equiv.) was added to a solution of 3-(RS)-aminomethyl-1-(2,3-dichlorobenzyl)-pyrrolidine (13 mg, 0.05 mmol), 2-[5-(3-methoxyphenyl)pyrimidin-2-ylamino]acetic acid (16 mg, 0.06 mmol, 1.2 equiv.), 1-hydroxybenzotriazole hydrate (10 mg, 0.08 mmol, 1.5 equiv.) and diisopropylethylamine (22 mL, 0.13 mmol, 2.5 equiv.) in dimethyl formamide (0.5 mL). The reaction mixture was shaken at room temperature overnight. The reaction mixture was quenched with methanol (0.3 mL), then purified directly by reverse phase preparative HPLC to give N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-[5-(4-methoxyphenyl)pyrimidin-2-ylamino]acetamide HCl salt (11 mg).

Provenance & Evidence