4-Methylmorpholine → HCID 57687105, compound

Participants

Reaction Steps

A mixture of 4-(6-amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)benzoic acid (100 mg) N,N-dimethylethane-1,2-diamine (0.036 ml), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (145 mg) and 4-methylmorpholine (0.066 ml) in NMP (1 ml) was stirred at room temperature for 15 hours. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (5 microns silica, 30 mm diameter, 150 mm length) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions were evaporated to dryness to afford the title compound (38 mg) as a solid; NMR Spectrum: (DMSOd6) 2.19 (s, 6H), 2.42 (t, 2H), 3.35-3.42 (m, 2H), 7.54 (dd, 1H), 7.86 (d, 2H), 7.93 (bs, 2H), 7.95 (d, 2H), 8.30 (dd, 1H), 8.41 (dd, 1H), 8.45 (t, 1H), 8.59 (d, 1H), 8.71 (d, 1H); Mass spectrum: M+H+: 403. RT: 1.73

Provenance & Evidence