Methanesulfonyl chloride → 5-(Azidomethyl)-2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole

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Reaction Steps

N,N-Diisopropylethylamine (3.22 g, 24.88 mmol, 5 eq) and methanesulfonyl chloride (0.855 g, 7.47 mmol, 1.5 eq) are successively and slowly added at 0° C. to a solution of [2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanol a3 (1.33 g, 4.98 mmol, 1 eq) in dichloromethane (30 ml). Sodium azide (0.485 g, 7.47 mmol, 1.5 eq) in suspension in DMF (5 ml) is added at 0° C., then warmed up to room temperature and the reaction mixture is stirred overnight. After hydrolysis (H2O) and extraction with diethylether, the combined organic layers are dried over MgSO4, filtered and evaporated under reduced pressure to afford 1.45 g of 5-(azidomethyl)-2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazole a18.

Provenance & Evidence