C(OC([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=O)(C)(C)C.[I-].[H-].[Na+].Br[CH2:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([Cl:30])=[CH:25][N:26]=[N:27]2)=[CH:22][CH:21]=1>C1COCC1>[Cl:30][C:24]1[C:23]2[C:28](=[CH:29][C:20]([CH2:19][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]3=[O:14])=[CH:21][CH:22]=2)[N:27]=[N:26][CH:25]=14-(t-Butyloxycarbonyl)-piperazin-2-one (0.6 g, 3.0 mmol), EXAMPLE 40, is dissolved in THF (80 mL), cooled in an ice bath and treated with tretrabutylammonium iodide (0.23 g, 0.62 mmol) and 60% sodium hydride (0.12 g, 3.0 mmol). The reaction mixture is stirred at ° C. for 40 minutes then treated dropwise with a solution of 7-bromomethyl-4-chlorocinnoline (10.7 g, 2.7 mmol), Example 15, in THF (20 mL). The resulting solution is warmed to ambient temperature over 2 hours. The solution is evaporated to dryness and the residue is taken up in ethyl acetate and 10% aqueous sodium bicarbonate solution. The organic layer is separated, washed with water, dried (sodium sulfate) and concentrated. The residue is chromatographed (ethyl acetate) to yield the title compound (0.6 g, 1.6 mmol). A portion of this material (0.21 g, 1.26 mmol) is dissolved in THF (˜4 mL) and treated with a saturated solution of HCl in ethyl acetate (50 mL) at room temperature for 2 hours. The solution is filtered and concentrated to a residue (0.14 g, 0.4 mmol). MS m/z: M+=275; 1H NMR (CD3OD, 300 MHz) δ9.15 (d, 1H), 8.5 (d, 1H), 8.25 (s, 1H), 8.15 (d, 1H), 8.0 (d, 1H), 5.0 (s, 2H), 4.1 (s, 2H), 3.7-3.8 (m, 2H), 3.6-3.7 (m, 2H).
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