[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.CN(C(O[N:28]1N=N[C:30]2[CH:31]=[CH:32]C=N[C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(N)CCC>CN(C)C=O.C(OCC)(=O)C>[CH2:29]([NH:28][C:16]([C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=3)=[N:11][C:10]=2[CH:12]=1)=[O:18])[CH2:30][CH2:31][CH3:32]To 2-p-tolylbenzo[d]oxazole-5-carboxylic acid (100 mg, 0.39 mmol) in dry dimethylformamide (10 mL) was added HATU (165 mg, 0.44 mmol) and diisopropylethylamine (206 μL, 1.18 mmol). The mixture was then stirred at room temperature for 10 min. Butan-1-amine (43 μL, 0.44 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic layer was washed three times with water. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 40:60 v/v to afford 26 mg (11%) of the title compound (LCMS RT=6.81 min, MH+ 309.1)
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