[B-](F)(F)(F)F.C[CH2:7][O:8][C:9]([C:11]([C:21]#[N:22])=NOC(N(C)C)=[N+](C)C)=O.C(N(CC)C(C)C)(C)C.[Br:32][C:33]1[S:37][C:36]([C:38]([OH:40])=O)=[C:35]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:34]=1.CONC1C=C[C:55]([O:58][CH2:59][CH2:60][N:61]2[CH2:65][CH2:64][CH2:63][CH2:62]2)=[CH:54][CH:53]=1>CN(C=O)C.C(OCC)(=O)C>[C:45]([O:44][C:42](=[O:43])[NH:41][C:35]1[CH:34]=[C:33]([Br:32])[S:37][C:36]=1[C:38](=[O:40])[NH:22][C:21]1[CH:53]=[CH:54][C:55]([O:58][CH2:59][CH2:60][N:61]2[CH2:62][CH2:63][CH2:64][CH2:65]2)=[C:9]([O:8][CH3:7])[CH:11]=1)([CH3:48])([CH3:47])[CH3:46]TOTU (327.3 mg) and N,N-diisopropylethylamine (122.8 mg) were added to a mixture of 5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid (306.1 mg), methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylamine (224.5 mg) in DMF (3.8 mL). The reaction mixture was stirred at room temperature overnight. Ethyl acetate was then added, and the organic phase was washed with 10% strength citric acid and saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated. The product with the molecular weight of 539.11 (C23H30BrN3O5S) was obtained in this way; MS (ESI): 540, 542 (M+H+).
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