Dimethylformamide → HCID 86642470, compound

Participants

Reaction Steps

To a solution of 6-(5-naphthalen-2-ylmethyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)pyridine-5-carboxylic acid (0.24 g, 0.6 mmol) in DMF (5 ml) were added HOBt (0.26 g, 1.7 mmol), EDCl (0.303 g, 1.6 mmol), DIPEA (1 ml, 5.8 mmol), and intermediate D (1 ml, 7.4 mmol). The mixture was stirred overnight and then poured into Et2O (250 ml). This was washed with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml). The extract was then dried (MgSO4), concentrated and purified by flash column chromatography (4% MeOH-DCM) to yield the title compound (0.199 g, 58%). 1H NMR (300 MHz, d6-DMSO) δ: 11.17 (1H, br s), 8.50 (1H, d, J=2.1 Hz), 7.81-7.90 (4H, m), 7.77 (1H, s), 7.42-7.50 (3H, m), 6.52 (1H, d, J=8.8 Hz), 4.95 (2H, q, J=7.0 Hz), 3.61-3.74 (6H, m), 2.88-2.99 (2H, m), 2.60-2.69 (2H, m), 1.72-1.84 (1H, m), 1.31 (3H, d, J=5.1 Hz), 0.86 (6H, d, J=6.6 Hz).

Provenance & Evidence