Triethylamine → HCID 136216271, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of triphosgene (0.017 g, 0.056 mmol) and 3-amino-2-methylpyridine (0.018 g, 0.17 mmol) in anhydrous THF (5 mL) was added dropwise triethylamine (0.14 mL, 1 mmol), at about 0° C. After stirring for about 5 min at about 0° C., 1-methyl-4-(4-piperidyl)-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepine dihydrochloride (0.07 g, 0.17 mmol, Preparation #4) was added at about 0° C. Subsequently, the mixture was stirred for about 1 h and allowed to come to rt. Then the mixture was diluted with ethyl acetate (10 mL), washed with water (10 mL) and brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, DCM/methanol/ammonium hydroxide 92:7.5:0.5) to give N-(2-methyl-3-pyridyl)-4-[1-methyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepin-4-yl]piperidine-1-carboxamide (0.03 g, 0.065 mmol, 26%) as an off white solid: LC-MS (Table 1, Method b) Rt=2.00 min; m/z 464 (M+H)+.

Provenance & Evidence