N,N-Dimethylethylenediamine → Trans 2-(2-(N,N-dimethylamino)ethyl)aminocarbonyl-4-phenylmethylcarbonylamino-5,7-dichloro-1,2,3,4-tetrahydroquinoline
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH2:5][C@H:6]([C:13]([O:15]C)=O)[NH:7]2.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>>[CH3:27][N:28]([CH2:29][CH2:30][NH:31][C:13]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)=[O:15])[CH3:32]Participants
3
Procedure
Trans 5,7-dichloro-2-methoxycarbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (Example 37a) (0.3 g) was dissolved in N,N-dimethylethylenediamine (30 ml) and allowed to stand at room temperature for 6 h. After this time the reaction mixture was filtered and the solvent was removed under vacuum. The residue was dissolved in ethyl acetate (100 ml) and washed with water (100 ml) then brine (100 ml). The organic solution was dried (MgSO4), filtered and concentrated in vacuo to give a solid which was triturated with diethyl ether and collected by filtration to give the title compound (0.19 g) as a colourless solid, m.p. 158°-159° C.; δ (360 MHz, DMSO) 1.54 (1H, ddd, J=13.0, 12.5 and 4.0 Hz, CHACHBHCCHD), 2.08 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 2.16 (6H, s, N(CH3)2), 2.33 (2H, t, J=6.7 Hz, CH2CH2N(CH3)2, 3.21 (2H, m, CH2CH2N(CH3)2), 3.37 (1H, d, J=14.0 Hz, CHEHFPh), 3.47 (1H, d, J=14.0 Hz, CHEHFPh), 3.74 (1H, dm, J=12.5 Hz, CHACHBHCCHD), 4.99 (1H, m, CHACHBHCCHD), 6.66 (1H, d, J=1.9 Hz, 6-H or 8-H), 6.79 (2H, m, 6-H or 8-H and ArNH), 7.26 (5H, m, ArH), 8.01 (1H, br, s, CONHCH2CH2N(CH3)2), 8.44 (1H, d, J=7.2 Hz, CHDNHCO); m/e 488 (M+); Found C, 58.47; H, 5.84; N, 12.39 C22H26Cl2N4O2 requires C, 58.80; H, 5.83; N, 12.47%.