[CH3:1][S:2]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C@H:7]([NH:16][C:17]2[C:18](=[O:30])[N:19]([CH2:24][C:25]([O:27]CC)=[O:26])[C:20]([Cl:23])=[CH:21][N:22]=2)[CH2:6]1)(=[O:4])=[O:3].[OH-].[Na+].Cl>CCO>[CH3:1][S:2]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C@H:7]([NH:16][C:17]2[C:18](=[O:30])[N:19]([CH2:24][C:25]([OH:27])=[O:26])[C:20]([Cl:23])=[CH:21][N:22]=2)[CH2:6]1)(=[O:4])=[O:3]A solution of 3-(1-methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone from step 11 above (0.20 g, 0.47 mmol) and aqueous NaOH (0.18 mL of a 4.0 N solution, 0.71 mmol) in EtOH (7 mL) was stirred at ambient temperature for 2 h. Aqueous HCl (0.12 mL of a 6.0 N solution, 0.72 mmol) was added, and the solvents were removed in vacuo to give the title compound as an amorphous solid containing NaCl (0.2 g, HPLC RT=3.99 min, method A).
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