[C:1](/[N:3]=[C:4](\SC)/[NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1)#[N:2].Cl.[NH2:17][OH:18].C(N(CC)CC)C>CN(C=O)C>[Cl:13][C:8]1[CH:7]=[C:6]([NH:5][C:4]2[N:3]=[C:1]([NH2:2])[O:18][N:17]=2)[CH:11]=[C:10]([Cl:12])[CH:9]=1In a 5 mL microwave vial, (Z)-methyl N′-cyano-N-(3,5-dichlorophenyl)carbamimidothioate (156 mg, 0.6 mmol, Eq: 1.00), hydroxylamine hydrochloride (347 mg, 5 mmol, Eq: 8.33) and triethylamine (506 mg, 697 μl, 5 mmol, Eq: 8.33) were combined with DMF (6 ml) to give a white suspension. The vial capped and stirred in a 50° C. oil bath for 3.5 hours. The reaction was concentrated in vacuo and the crude material was purified by preparative TLC (silica gel, 1.0 mm, 9:1 DCM/MeOH) to give product, was recrystallized from EtOH then dried in vacuo (80° C., 2 torr, overnight) to give 15 mg (10%) of desired product as a white solid.
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