[CH:1]1([C:5]2[S:9][C:8]([NH2:10])=[N:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:18]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][C:29](O)=[O:30])=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)(Cl)Cl>[CH:1]1([C:5]2[S:9][C:8]([NH:10][C:29](=[O:30])[CH2:28][C:24]3[CH:23]=[C:22]4[C:27](=[CH:26][CH:25]=3)[N:18]=[CH:19][CH:20]=[CH:21]4)=[N:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1A solution of 5-cyclobutyl-thiazol-2-ylamine (Preparation 2; 30 mg, 0.195 mmol) was treated with triethylamine (81 μl, 0.585 mmol), 6-quinolylaceticacid (40 mg, 0.214 mmol) and propylphosphonic acid cyclic anhydride (T3P, 126 mL, 0.214 mmol). After 2 hours, an additional 0.2 equiv. of T3P (22 μl) was added and the reaction was complete by TLC after 15 minutes. The reaction mixture was diluted with CHCl3, was washed with saturated aqu. NaHCO3, and was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (40:1 CHCl3—MeOH) to afford 55 mg of N-(5-cyclobutyl-thiazol-2-yl)-2-quinolin-6-yl-acetamide, the title compound, as a white solid.
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