4-Methylmorpholine → HCID 21893751, compound

Participants

Reaction Steps

A solution of the tert-butyl 4-({4-[5-(4-methoxyphenyl)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)tetrahydro-2H-pyran-4-carboxyate acid trifluoroacetate product from Part C (266 mg, 0.57 mmol), N-hydroxybenzotriazole (97.2 mg, 0.72 mmol), 4-methylmorpholine (0.20 mL, 1.8 mmol), O-tetrahydro-2H-pyran-2-yl-hydroxyamine (105 mg, 0.9 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (161 mg, 0.84 mmol) in DMF (11 mL) was stirred at ambient temperature under an argon atmosphere for 18 hr. Afterward, the solution was concentrated in vacuo, diluted with water (20 mL), and extracted with ethyl acetate. The organic layer was washed with water, washed with saturated NaCl, dried over MgSO4, and concentrated in vacuo to produce a solid. Chromatography (on silica, 5% methanol/acetate) produced the desired compound in the form of a solid (128 mg, 39%). MS H+ calculated for C26H35N5SO7: 562; found: 562.20

Provenance & Evidence