[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([S:9](Cl)(=[O:11])=[O:10])=[CH:8][C:4]=2[CH:3]=1.[O-:15][C:16]#[N:17].[Na+].N1C=CC=CC=1.Br.[NH2:26][C:27]1[S:28][C:29]([Br:32])=[CH:30][N:31]=1>C(#N)C>[Br:32][C:29]1[S:28][C:27]([NH:26][C:16]([NH:17][S:9]([C:7]2[S:6][C:5]3[CH:13]=[CH:14][C:2]([CH3:1])=[CH:3][C:4]=3[CH:8]=2)(=[O:11])=[O:10])=[O:15])=[N:31][CH:30]=1
To a suspension of 5-methyl-benzo[b]thiophenesulfonyl chloride (Maybridge, CAS: 90273-30-6, 0.37 g) in acetonitrile (5.0 mL) were added sodium cyanate (0.163 g) in one portion and pyridine (0.60 mL). The reaction mixture was stirred at rt for 3 h, then 2-amino-5-bromothiazole hydrobromide (0.286 g) was added in one portion. The mixture was stirred at rt for 4 h and quenched with 70% acetic acid (2.4 mL) and water (4.0 mL). The suspension was filtered, washed with waterlethanol and water, dried over P2O5 under high vacuum to obtain the desired compound (0.372 g) as a creamy solid. MS (ISN): m/e 430.1, 432.0 (M−H)−
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