[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:34]=[C:33]([C:35](O)=[O:36])[CH:32]=[N:31][CH:30]=2)=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:18]1([CH2:17][NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[C:5]([CH3:21])=[CH:4][CH:3]=[C:2]([NH:1][C:35]([C:33]4[CH:32]=[N:31][CH:30]=[C:29]([C:26]5[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=5)[N:34]=4)=[O:36])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]15′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl4-carboxamide (75 mg, 0.27 mmol), 6-(4fluorophenyl)pyrazine-2-carboxylic acid (58.4 mg, 0.27 mmol), HATU (101.5 mg, 0.27 mmol), HOBT (36 mg, 0.27 mmol) and DIPEA (140 μl, 0.80 mmol) in DMF (3 ml) were stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (150 ml), washed with hydrochloric acid (0.5M, 2×20ml), aqueous sodium hydrogen carbonate (20 ml) and dried (magnesium sulphate). Evaporation of the solvents under vacuum gave N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-6-(4-fluorophenyl)pyrazine-2-carboxamide (117 mg, 91%). NMR; δH [2H6]—DMSO 10:64,(1H, s), 9.52,(1H, s), 9.20,(1H, s), 8.63,(1H, t), 8.54,(2H, m), 7.95,(2H, d), 7.88,(1H, dd), 7.78,(1H, d), 7.48,(2H, d), 7.42,(2H, t), 7.35,(1H, d), 3.17,(2H, t), 2.23,(3H, s), 1.05,(1H, m), 0.24,(2H, m). LCMS: retention time 3.65 min, MH+481.
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