Trifluoroacetic acid → HCID 73214322, compound

Participants

Reaction Steps

In THF (20 mL) were dissolved 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-pyrimidine-5-carboxylic acid (150 mg, 0.40 mmol), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (128 mg, 0.60 mmol) and HATU (182 mg, 0.48 mmol). DIEA (0.20 mL, 1.2 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 8 h. The reaction mixture was concentrated, followed by addition of water and extraction with DCM. The organic phase was dried, concentrated, and purified by silica gel column chromatography (DCM/methanol=50/1) to give a white solid. The product was dissolved in DCM (10 mL), and trifluoroacetic acid (1 mL) was added. The reaction was conducted at ambient temperature for 4 h. Then the reaction mixture was adjusted to a pH of 9 with saturated aqueous sodium bicarbonate. The organic phase was dried and the solvent was removed by rotary evaporation to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(piperdin-4-ylmethyl)pyrimidine-5-formamide (34 mg, 18% yield).

Provenance & Evidence