Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1.[CH3:19][NH:20][CH3:21].C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:19][N:20]([CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1)[CH3:21]To 2-(chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole (0.399 g, 1.48 mmol) in dioxane (10 mL) was added dimethylamine (1.87 mL, 40% weight in H2O, 14.8 mmol). The reaction was heated at 60° C. overnight. The reaction was poured into half saturated NaHCO3, extracted with DCM and EtOAc, dried (MgSO4) and concentrated. The residue was taken up in EtOAc (20 mL) and Pd on carbon was added in one portion. The mixture was stirred at rt under H2 (1 atm.) until complete by TLC. The reaction was filtered through Celite® and concentrated to provide the title compound of step D (0.326 g, 1.32 mmol, 89% over two steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.18-2.23 (m, 6H), 3.67-3.72 (m, 2H), 3.76-3.82 (m, 3H), 5.47-5.56 (m, 2H), 6.64-6.72 (m, 1H), 7.25 (d, J=2.0 Hz, 1H), 7.30 (dt, J=8.1, 2.1 Hz, 1H).
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