Triethylamine → tert-butyl N-({[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)glycinate

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Reaction Steps

N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide (Intermediate 6) (160 mg; 0.48 mmol; 1 eq) is dissolved in DMF (8 ml). A solution of glycine tert-butyl ester (63.5 mg; 0.48 mmol; 1 eq) in DMF (1 ml) and triethylamine (74 μl; 0.53 mmol; 1.10 eq) are added. After less than 1 min the mixture becomes homogeneous. After 45 min, the reaction is complete. DMF is removed under reduced pressure to afford 235.8 mg of a dark brown solid, which is purified by preparative HPLC. The purified fractions are neutralized with NaHCO3 sat. solution and the desired product is extracted with DCM. The combined organic layers are dried over MgSO4, filtered and concentrated, affording Compound (65) as a brown solid (27.30 mg; 14%).

Provenance & Evidence