4-Methylmorpholine → HCID 67773174, compound

Participants

Reaction Steps

3-Chloro-4-fluorobenzoic acid (0.156 g, 0.89 mmol), TBTU (0.334 g, 1.04 mmol) and NMM (0.204 mL, 1.86 mmol) was mixed in DCM (10 mL). After 10 min at rt was (S)-1-cyclopropyl-N-methyl-2-(pyrrolidin-1-yl)ethanamine (Compound M3) (0.125 g, 0.74 mmol) added. The resultant mixture was stirred at rt for 48 h. To the mixture was 1.4 N KOH (5 mL) added. The organic phase was isolated, filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (130 mg, 54%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.03, 0.16-0.62, 0.95, 1.50-1.74, 2.14-2.41, 2.47-2.51, 2.65-3.06, 3.84, 7.29, 7.46. Total no of protons: 22. HRMS (M+H)+: calculated 325.1483. found 325.1475.

Provenance & Evidence