[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([OH:16])=O)=[C:9]2[CH3:17])=[CH:4][CH:3]=1.[NH2:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.Cl.[NH2:42][OH:43]>ClCCl.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([C:14]([NH:25][CH2:24][C:23]3[CH:26]=[CH:27][C:20]([C:19](=[N:42][OH:43])[NH2:18])=[CH:21][CH:22]=3)=[O:16])=[C:9]2[CH3:17])=[CH:6][CH:7]=130 g of 1-(4-fluorophenyl)-2,5-dimethyl-pyrrole-3-carboxylic acid was reacted with 1 equivalent of 4-(aminomethyl)benzonitrile, in the presence of 1.1 equivalents of oxalyl chloride, 3 equivalents of triethylamine in dichloromethane at room temperature for 3 h. The product was then reacted with hydroxylamine hydrochloride (3 equivalents) in ethanol at 80° C. for 3 h. The target compound (36 g) was obtained as a tan-colored powder following solvent removal by evaporation. Purity assessed by HPLC was 97.8%, and mass was verified by LC/MS/MS (predicted m+1=381.2, obtained m+1=381.2). 1H-NMR (DMSO): δ 1.93 (3H), 2.21 (3H), 4.39-4.40 (2H), 5.76 (2H), 6.42 (1H), 7.26-7.28 (2H), 7.35-7.40 (4H), 7.60-7.62 (2H), 8.22 (1H), 9.56 (1H).
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