1-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amine → tert-butyl 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl-3-((dimethylamino)methylene)-4-oxopiperidine-1-carboxylate (10.2 g, 40.15 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (8.55 g, 42.16 mmol) were heated at 130° C. for 48 hours. The reaction mixture was cooled and the crude product was purified by flash column chromatography (SiO2, gradient from 100% CH2Cl2 to 5% MeOH in CH2Cl2) to give the desired product tert-butyl 3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate as an off white solid (3.5 g, 22%). 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.99 (s, 1H), 7.14 (d, J=8.4 Hz, 2H), 7.81 (d, J=8.4 Hz, 2H), 5.62 (s, 2H), 4.71 (s, 2H), 3.82-3.74 (m, 5H), 3.07 (t, J=6.0 Hz, 2H), 1.44 (s, 9H). LCMS [M+H]: 395.

Provenance & Evidence