1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine → 5-methyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepin-1-yl}aniline
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:15][CH2:14]1>CCOC(C)=O.CO>[CH3:1][C:2]1[C:3]([N:13]2[CH2:19][CH2:18][CH2:17][N:16]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:23])=[O:24])[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]hexahydro-1H-1,4-diazepine (0.70 g, 1.9 mmol) was placed in a 200 mL high pressure vessel and dissolved in 40 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/C (0.51 g, 0.132 mmol) was added followed quickly by a rubber septum. The vial was evacuated and filled with N2 six times to remove any oxygen. The vial was then pressurized with H2 (60 psi). The solution stirred for 2 h. The vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to afford the title compound of step C (0.585 g, 1.71 mmol, 91%). 1H NMR (400 MHz, DMSO-d6) δ 6.54 (s, 1H), 6.38 (s, 1H), 4.27 (br. s., 2H), 3.67 (s, 3H), 3.24 (t, J=6.59 Hz, 2H), 3.02 (s, 3H), 2.86-2.97 (m, 6H), 2.75 (t, J=5.49 Hz, 2H), 2.68-2.73 (m, 2H), 2.05 (s, 3H), 1.74-1.81 (m, 2H).