[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5](=[N:7][OH:8])[NH2:6].[N:13]1[CH:18]=[C:17]([C:19]([Cl:21])=[O:20])[CH:16]=[N:15][CH:14]=1.N1C=C(C(O)=O)C=NC=1.C(Cl)(=O)C(Cl)=O>>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:19]([C:17]3[CH:18]=[N:13][CH:14]=[N:15][CH:16]=3)[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[F:12].[N:13]1[CH:18]=[C:17]([C:19]([Cl:21])=[O:20])[CH:16]=[N:15][CH:14]=1The titled compound was prepared according to the procedure of Method D using 3,4-difluoro-N′-hydroxybenzimidamide (Tyger) and pyrimidine-5-carbonyl chloride. The pyrimidine-5-carbonyl chloride was prepared by the reaction of pyrimidine-5-carboxylic acid (Maybridge, 138 mg, 1.0 mmol) with oxalyl chloride (Aldrich, 2 M, in CH2Cl2, 1.0 mL, 2.0 mmol) and a drop of dimethylformamide at room temperature over 1 hour with subsequent removal of volatiles under reduced pressure. 1H NMR (300 MHz, DMSO-d6) δ 7.72 (dt, J=10.5, 8.5 Hz, 1H), 7.94-8.05 (m, 1H), 8.11 (ddd, J=10.9, 7.7, 2.0 Hz, 1H), 8.12 (none, 1H), 9.51 (s, 1H), 9.54 (s, 2H) ppm; MS (DCI/NH3) m/z 261 (M+H)+.
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