Water → HCID 18008963, compound

Participants

Reaction Conditions

Reaction Steps

Benzoyl chloride (22 μl) was added to a stirred mixture of 3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-1,2,3,4-tetrahydro-quinoxalin-6-yl)-butyric acid ethyl ester (0.110 g, Reference Example 17) and triethylamine (87.8 μl) in tetrahydrofuran (10 ml) cooled to 0° C. under an argon atmosphere. The mixture was stirred for 1 hour at 0° C., then allowed to warm to 20° C., then stirred at this temperature for 2 hours and then treated with a further aliquot of benzoyl chloride (11 μl). After stirring overnight the reaction mixture was treated with water (20 ml) then extracted three times with ethyl acetate (25 ml). The combined extracts were dried over magnesium sulfate then evaporated (40° C., 40 mbar). The crude residue (147 mg) was subjected to flash chromatography on silica (20 g, 0.040-0.063 mm particle size) eluting with a mixture of dichloromethane and methanol (99:1, v/v) to give the title compound as a white foam (132 mg). TLC: RF 13/56 (cyclohexane:ethyl acetate, 9:1, v/v). 1H NMR [400 HMz, (CD3)2SO, at a temperature of 383° K.]: δ0.96 (d, J=7 Hz, 3H); 1.16 (t, J=7 Hz, 3H); 2.24 (d, J=7.5 Hz, 2H); 2.28 (s, 3H); 2.93 (m, 1H); 3.83 (s, 3H); 3.94 (m, 2H); 3.96 (s, 21H); 4.02 (m, 2H); 4.04 (q, J=7 Hz, 2H); 6.63 (broad s ,1H); 6.76 (broad d, J=8 Hz, 1H); 6.90 (broad s, 1H); 6.99 (m, 2H); from 7.10 to 7.20 (m, 4H); 7.34 (broad t, J=7.5 Hz, 2H); 7.41 (broad t, J=7.5 Hz, 1H); 7.57 (d, J=8 Hz, 1H); 7.67 (broad d, J=8 Hz, 1H); 8.02 (d, J=8.5 Hz, 1H); 8.16 (broad s, 1H); 8.24 (broad s, 1H). MS (EI): 648 (M+).

Provenance & Evidence