[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])[CH:22]=2)[CH2:17][CH2:16][CH2:15]1)C(=O)OC1C=CC=CC=1.O.[OH-].[Na+]>C(O)C.C(Cl)Cl>[CH3:1][NH:2][CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])[CH:22]=2)[CH2:17][CH2:16][CH2:15]1A solution of compound 5 (1.30 g, 2.991 mmol) in ethanol:H2O (30 mL, 3:1) was treated with NaOH (1.19 g, 29.916 mmol) at room temperature and the resulting solution was refluxed for 6 h. The reaction was brought to room temperature, diluted with CH2Cl2 (25 mL) and washed with brine (15 mL). The aqueous layer was extracted with more CH2Cl2 (2×20 mL) and combined CH2Cl2 layer was dried (Na2SO4). The solvent was evaporated and crude product was purified by column chromatography on silica gel (2 M NH3 in MeOH:CH2Cl2, 5:95 to 1:9) to obtain compound 44 (0.6 g, 64%) as a solid. 1H NMR (DMSO-d6) δ 7.69 (d, 1H, J=3.0 Hz), 7.57 (dd, 1H, J=0.9, 5.1 Hz), 7.07 (dd, 1H, J=3.6, 5.1 Hz), 6.78 (d, 1H, J=7.5 Hz), 6.22 (brs, 2H), 6.08 (d, 1H, J=1.2 Hz), 5.99 (dd, 1H, J=1.5, 7.6 Hz), 3.27-3.23 (m, 4H), 2.68-2.61 (m, 4H), 2.31 (s, 3H), 1.87-1.80 (m, 2H); ESI-MS (m/z, %): 315 (MH+, 100); ESI-HRMS calculated for C17H23N4S (MH+), calculated: 315.1637; observed: 315.1652; HPLC purity 98.67% by area.
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