Triethylamine → (3S)-3-methyl-4-(((2S)-4-(1,3-thiazol-2-ylsulfonyl)-2-piperazinyl)methyl)morpholine

Participants

Reaction Conditions

Reaction Steps

A 50-mL round-bottomed flask was cooled to 0° C. and charged with (3S)-3-methyl-4-((2R)-2-piperazinylmethyl)morpholine (100 mg, 0.5 mmol, Example 82, Step 2), CH2Cl2 (5 mL) and triethylamine (0.07 mL, 0.5 mmol). Thiazole-2-sulfonyl chloride (92 mg, 0.5 mmol, Bioorg. Med. Chem., 2006, 14, 6628) was added and after 10 min the reaction was concentrated and acidified with 4 N HCl in dioxane (5 mL). The HCl salt was collected after filtration and the crude material was purified via column chromatography (40 g silica gel, 0 to 10% (2M NH3 in MeOH) in CH2Cl2) to give (3S)-3-methyl-4-(((2S)-4-(1,3-thiazol-2-ylsulfonyl)-2-piperazinyl)methyl)morpholine (210 mg).

Provenance & Evidence