Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[C:4]1=[O:17].C(N(CC)CC)C.[N:25]1[C:34]2[C:29](=[CH:30][C:31]([S:35](Cl)(=[O:37])=[O:36])=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>CC#N.CCOC(C)=O>[C:12]([C:11]1[CH:10]=[C:9]([CH:16]=[CH:15][CH:14]=1)[CH2:8][N:5]1[CH2:6][CH2:7][C@H:3]([NH:2][S:35]([C:31]2[CH:30]=[C:29]3[C:34](=[CH:33][CH:32]=2)[N:25]=[CH:26][CH:27]=[CH:28]3)(=[O:36])=[O:37])[C:4]1=[O:17])#[N:13]3-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride (0.32 g, 1.26 mmol) is suspended in 15 mL of CH3CN. To the solution is added triethylamine (0.384 g, 3.78 mmol) followed by quinoline-6-sulfonyl chloride (0.25 g, 0.99 mmol). After stirring for 1.5 hours, the solution is diluted with EtOAc and washed with 0.1 N aqueous HCl, water and saturated NaCl solution. The organic layer is dried over Na2SO4, filtered and concentrated. The crude residue is purified by column chromatography (4% MeOH/CH2Cl2) to afford the title compound (0.146 g, 0.36 mmol) and as a solid.
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