4-Methylmorpholine → HCID 67995327, compound

Participants

Reaction Steps

A solution of 2-((3-(1-carbamoyl-7-((2-(trimethylsilyl)ethoxy)carbonylamino)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-chlorobenzoic acid (0.343 g, 0.533 mmol), DIPEA (0.279 mL, 1.599 mmol), N-methylmorpholine (0.469 mL, 4.26 mmol) and BOP (0.613 g, 1.386 mmol) in DMF (5.33 mL) under nitrogen was heated at 45° C. for 45 min. The reaction was cooled to room temperature, dissolved in EtOAc (100 mL) and washed with water (3×25 mL) and brine (25 mL), dried over MgSO4, and concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 40 g column eluting with 30-75% EtOAc/hexanes. Appropriate fractions were collected and concentrated in vacuo to give the desired product (0.140 g, 0.224 mmol, 41.9% yield) as a light orange solid.

Provenance & Evidence