Triethylamine → N-[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]acetamide

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Reaction Steps

N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide (Intermediate 1)(1.0 g; 2.79 mmol; 1 eq.) is dissolved in EtOH (25 ml). Triethylamine (980 μl; 6.98 mmol; 2.50 eq.) and 2-cyanothioacetamide (Aldrich)(279.7 mg; 2.79 mmol; 1 eq.) are added. The mixture is stirred 2 h30 at rt. Solvents are evaporated and the crude product is purified by flash chromatography, with cyclohexane/EtOAc gradient as eluent. Compound (3) is isolated as a white-off powder (680.3 mg; 88%). HPLC (method A), Rt 2.30 min (purity: 92.79%). Compound (3) is further crystallized in EtOAc, affording a new batch as colorless needles (412.60 mg; 52.75%). 1H NMR (DMSO-d6, 300 MHz) δ 2.13 (s, 3H), 2.47 (s, 3H), 4.61 (s, 2H), 7.71 (s, 1H), 12.12 (br s, 1H). M− (ESI): 277; M+ (ESI): 279. HPLC (method A), Rt: 2.28 min (purity: 99.5%).

Provenance & Evidence