[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([NH2:19])[C:7]([NH2:18])=[CH:8][C:9]=1[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:20](=S)=[S:21].CC(O)=O>CCO.O>[Cl:3][C:4]1[C:9]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]2[NH:18][C:20](=[S:21])[NH:19][C:6]=2[CH:5]=1A 2 mL Biotage™ microwave vial was charged with solid KOH (19.4 mg, 0.345 mmol), water (0.2 mL), a solution of compound 1-2 (55.8 mg, 0.230 mmol) in EtOH (1.2 mL) and carbon disulfide (69 uL, 1.2 mmol). The vial was capped and stirred at rt until KOH dissolved, and then heated in a microwave synthesizer (Biotage Initiator™) at 110° C. for 10 min. Contents of the vial were transferred to a 20 mL scintillation vial, diluted with water (8 mL) and acidified by the dropwise addition of 10% aqueous AcOH. The resulting suspension was centrifuged, the supernatant was decanted and the resulting brownish precipitate was washed with 10% aqueous AcOH (3 mL) and water (three times 3 mL). The precipitate was dissolved in EtOAc and passed through a short plug of neutral alumina. The EtOAc solution was evaporated to dryness in vacuo to give the crude product as brownish solid. LR-MS (API-ES): calculated for C15H9ClN2S 284.0, observed m/e 285.0 (M+H)+. (Rt 2.94 min). The crude product was used in the next step without further purification.
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