[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:14]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[Cl:27][C:28]1[C:33]([Cl:34])=[CH:32][C:31]([NH2:35])=[C:30]([NH2:36])[CH:29]=1.CI>C(Cl)Cl.CCO>[Cl:27][C:28]1[C:33]([Cl:34])=[CH:32][C:31]2[NH:35][C:14]([NH:11][C:10]3[CH:9]=[CH:8][C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:13][CH:12]=3)=[N:36][C:30]=2[CH:29]=1To a stirring solution of 4-cyclohexylaniline (10 mmol, 1.75 g) and DIEA (21 mmol, 3.65 mL) in CH2Cl2 (10 mL) at 0° C. was added thiophosgene (10 mmol, 700 μL) dropwise. The solution was allowed to reach ambient temperature for 1 h, and 4,5-dichloro-1,2-phenylenediamine (10.5 mmol, 1.86 g) was added. The reaction mixture was heated to reflux for 2 h, then concentrated in vacuo. The residue was taken up in a solution of EtOH (5 mL) and MeI (20 mmol, 1.25 muL), heated at 40° C. for 16 h, and concentrated in vacuo. Flash chromatography on silica eluting with 18-25% EtOAc in hexanes afforded the product as a red solid. LC-MS (ESI, Method C): 3.47 min, m/z 360.2 (M+1).
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