[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[C:16]([O:29][CH3:30])[C:17]([O:19][C:20]4(C(O)=O)C=CC=CN4)=[CH:18][C:11]=3[N:10]=2)=[CH:4][C:3]=1[CH3:31].[N:32]1([CH2:37][CH2:38][NH2:39])[CH2:36][CH2:35][CH2:34][CH2:33]1.CN(C([O:47]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:67]([CH2:71][CH3:72])[CH:68]([CH3:70])[CH3:69])(C)C>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[C:16]([O:29][CH3:30])[C:17]([O:19][C:20]4[CH:72]=[CH:71][N:67]=[C:68]([C:69]([NH:39][CH2:38][CH2:37][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[O:47])[CH:70]=4)=[CH:18][C:11]=3[N:10]=2)=[CH:4][C:3]=1[CH3:31]To 4-(2-{[4-bromo-3-methylpheylamino)-6-methoxy-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid(1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was concentrated and preparative chromatography yielded [4-(2-{(4-bromo-3-methylphenyl)amino}-6-methoxy-1-methylbenzimidazol-5-yloxy)(2-pyridyl)]-N-(2-pyrrolidinylethyl)carboxamide. MS: MH+=579.
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