[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:24]([OH:26])=O)=[CH:11][C:12]3[N:16]([CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[CH:15]=[N:14][C:13]=3[C:22]=2[F:23])=[C:4]([CH3:27])[CH:3]=1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=[CH:58][CH:59]=[CH:60][C:55]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.C1([N:74](C)[OH:75])CC1>C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[CH:59]1([CH2:58][O:75][NH:74][C:24]([C:10]2[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[CH3:27])=[C:22]([F:23])[C:13]3[N:14]=[CH:15][N:16]([CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[C:12]=3[CH:11]=2)=[O:26])[CH2:60][CH2:55]16-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid 10d (0.390 g, 0.902 mmol) is dissolved in 1:1 THF/methylene chloride (6 mL) and Hunig's base (0.346 mL, 1.985 mmol) is added followed by PyBOP (0.563 g, 1.083 mmol). After 10 minutes, cyclopropyl methyl hydroxylamine hydrochloride (0.134 g, 1.083 mmol) is added. After 16 hours, the reaction mixture is diluted with ethyl acetate and washed with 0.1 N HCl, saturated NaHCO3, and brine. The organic layer is dried (Na2SO4) and concentrated under reduced pressure. The crude yellow residue is purified by FCC eluted with ethyl acetate to give 0.315 g (70%) pure desired product as a yellow solid: MS APCI (+) m/z 503, 501 (M+1 Br pattern) detected.
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