[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@H:13]([NH2:15])[CH2:12]1.[Cl:16][C:17]1[C:22](Cl)=[N:21][CH:20]=[CH:19][N:18]=1>C(O)(C)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:12][C@H:13]([NH:15][C:22]2[C:17]([Cl:16])=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:14]1Trans-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (intermediate 11, 0.058 g, 0.264 mmol) and 2,3-dichloropyrazine (0.035 ml, 0.336 mmol) were suspended in isopropanol (1 mL) in a microwave vial. The mixture was heated at 150° C. for 90 minutes. The mixture was evaporated to dryness under reduced pressure and purified using silica chromatography (hexane to ethyl acetate gradient) to give trans-N1-(benzo[d]thiazol-2-yl)-N3-(3-chloropyrazin-2-yl)cyclobutane-1,3-diamine (0.0594 g, 0.179 mmol, 67.7% yield) as an oil.
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