CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:34]1([C:40]([OH:42])=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.[Br:43][C:44]1[CH:53]=[CH:52][C:47]2[N:48]=[C:49]([NH2:51])[S:50][C:46]=2[CH:45]=1>C(Cl)Cl>[Br:43][C:44]1[CH:53]=[CH:52][C:47]2[N:48]=[C:49]([NH:51][C:40]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)=[O:42])[S:50][C:46]=2[CH:45]=1A mixture of Hunig's base (286 μl, 1637 μmol), HATU (830 mg, 2182 μmol) and cyclohexanecarboxylic acid (147 mg, 1146 μmol) was dissolved in 2.0 mL CH2Cl2 and stirred at room temperature for 10 min. 6-bromobenzo[d]thiazol-2-amine (250 mg, 1091 μmol) was added, and stirring was continued overnight. The solids were filtered and washed with CH2Cl2. The filtrate was concentrated, dissolved in CH2Cl2 and purified by silica gel chromatography using 100% CH2Cl2 to provide N-(6-bromobenzo[d]thiazol-2-yl)cyclohexanecarboxamide (290 mg, 78% yield) as a white solid. MS (ESI pos. ion) m/z calc'd for C14H15BrN2OS: 339.3/341.3. found 339.0/341.0.
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