Aluminium lithium hydride → 1-(3-Chloro-1-methyl-1H-pyrazol-4-yl)-8-(5-hydroxymethyl-6-methoxy-pyridin-3-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Participants

Reaction Steps

To a solution of 5-[1-(3-chloro-1-methyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-2-methoxy-nicotinic acid methyl ester (stage 200.1, 0.176 mmol) in THF (2 ml) cooled with an ice-bath was added dropwise a 1 M solution of LiAlH4 in THF (0.150 mmol). The reaction mixture was stirred for 1 h 15 min at rt, then quenched with water, diluted with EtOAc and filtered over Celite. The filtrate was washed with saturated aqueous NaHCO3, with water, with brine, dried over Na2SO4, filtered and evaporated. The residue was dissolved in MeOH/TFA and purified by preparative HPLC. The fractions containing pure product were basified with NaHCO3 and concentrated. The precipitate was filtered, washed with water (2×) and dried under vacuum to give the title compound as a white solid. (HPLC: tR 2.53 min (Method A); M+H=451 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.41 (s, 1H), 8.30-8.27 (m, 1H), 8.14-8.10 (m, 1H), 7.98-7.93 (m, 1H), 7.84-7.81 (m, 1H), 7.53-7.50 (m, 1H), 5.32 (t, 1H), 4.51 (d, 2H), 4.01 (s, 3H), 3.92 (s, 3H), 3.59 (s, 3H))

Provenance & Evidence