4-Methylmorpholine → HCID 67281838, compound

Participants

Reaction Steps

A mixture of 7-(methoxycarbonyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-2-carboxylic acid (0.15 g, 0.6 mmol), DMF (8 mL), N-methylmorpholine (66 μL, 0.6 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.23 g, 1.2 mmol) and 1-hydroxybenzotriazole (81 mg, 0.6 mmol) was stirred for 15 min and 4-amino-1-Boc-piperidine (144 mg, 0.72 mmol) was added. The reaction mixture was stirred at rt for 1 d. Water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 100% EtOAc/DCM) to afford to afford methyl 2-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (60 mg, 20%). LC-MS: (FA) ES+ 333.

Provenance & Evidence