Tetrahydrofuran → HCID 59619952, compound

Participants

Reaction Steps

A mixture of {4-[8-(6-Methoxy-pyridin-3-yl)-3-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-3-methyl-pyrazol-1-yl}-acetic acid TFA salt (Example 101, 60 mg, 0.107 mmol), TPTU (128 mg, 0.430 mmol) and DIPEA (0.094 ml, 0.537 mmol) in DMA (1.5 ml) was stirred under argon at rt for 20 min. Then dimethtylamine in THF 2 M (Aldrich, Buchs, Switzerland, 0.242 ml, 0.483 mmol) was added and the RM was stirred at rt for 3 h. The RM was directly purified by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 50:50). The fractions containing products were collected together and basified with NaHCO3 (0.3 g), before being concentrated. The resulting layer was extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid. (HPLC: tR 2.57 min (Method A); M+H=472 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.95 (s, 1H), 8.50-8.43 (m, 1H), 8.14-8.04 (m, 2H), 8.01-7.96 (m, 1H), 7.95-7.90 (m, 1H), 7-77-7.71 (m, 1H), 6.87-6.81 (m, 1H), 5.25-5.09 (m, 2H), 3.86 (s, 3H), 3.56 (s, 3H), 3.05 (s, 3H), 2.88 (s, 3H), 1.93 (s, 3H))

Provenance & Evidence