Hydrogen Bromide → HCID 131728331, compound

Participants

Reaction Conditions

Reaction Steps

N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N-(1-acetyl-1H-pyrazol-3-yl)acetamide (689.3 mg; 2.25 mmol; 1 eq.) is dissolved in AcOH (10 ml) and hydrobromic acid (39 μl; 0.22 mmol; 0.10 eq.). A solution of bromine (115 μl; 2.25 mmol; 1 eq.) in AcOH (2 ml) is added dropwise. The reaction mixture is stirred 3 h at rt and 2 h at 60° C. In order to complete the reaction, a solution of bromine (58 μl; 1.12 mmol; 0.50 eq.) in AcOH (2 ml) is added and the mixture is stirred 4 h at 60° C. It is cooled down to rt and the resulting precipitate is filtered, washed with cyclohexane and dried under reduced pressure to give, affording Intermediate 4 (695.7 mg; 73%). It is used in bis-thiazol synthesis as HBr salt or as parent, after 5 min treatment with Amberlyst A21 in DCM/MeOH mixture. 1H NMR (DMSO-d6, 300 MHz) δ 2.57 (s, 3H), 2.64 (s, 3H), 4.63 (s, 2H), 6.36 (d, J=6 Hz, 1H), 8.35 (d, J=6 Hz, 1H). M− (ESI): 342.96; M+ (ESI): 344.94. HPLC (Method A), Rt: 3.08 min (purity: 91.91%).

Provenance & Evidence