4-Methylmorpholine → HCID 24764639, compound

Participants

Reaction Steps

A 25 mL flask was charged with 60 mg 2-(pyridin-4-yl)acetic acid (0.35 mmol, 1.0 equiv), 150 mg 1-(4-tert-butylphenylsulfonyl)piperazine (0.53 mmol, 1.5 equiv), 378 mg O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU, 0.88 mmol, 2.1 equiv), and 119 mg 1-hydroxybenzotriazole hydrate (HOBT, 0.88 mmol, 2.1 equiv). The flask was then charged with 5 mL DMF, stirring was initiated (magnetic stirrer) and 0.97 mL N-methylmorpholine (NMM, 0.88 mmol, 2.1 equiv) was added in one portion to the suspension. After 12 h, the suspension was diluted with 20 mL sat. NaHCO3 and extracted (2×CH2Cl2). The CH2Cl2 solution was then dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2) gave the product as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.50 (d, J=5.2 Hz, 2H), 7.70 (d, J=8.5 Hz, 2 H), 7.55 (d, J=8.5 Hz, 2H), 7.09 (d, J=5.3 Hz, 2 H), 3.73 (m, 2 H), 3.65 (s, 2 H), 3.53 (m, 2 H), 2.99 (m, 2H), 2.89 (m, 2H), 1.36 (s, 3 H).

Provenance & Evidence