4-Bromobenzoic acid → HCID 67774063, compound

Participants

Reaction Steps

DIPEA (0.217 mL, 1.25 mmol) was added to a stirred suspension of 4-bromobenzoic acid (0.075 g, 0.37 mmol) and TBTU (0.120 g, 0.37 mmol) in DCM (2 mL) at rt. The suspension was stirred for 20 min before it was cooled on an ice-bath. A solution of (S)-1-(2-(methylamino)propyl)azetidin-3-ol (Compound M11) (0.06 g, 0.42 mmol) in THF (1.5 mL) was added over 10 min. The ice-bath was removed and the reaction was stirred at rt over night. DCM (3 mL) was added and the mixture was washed with NaHCO3 (8% aq., 3 mL). The aqueous layer was extracted with DCM (2×3 mL). The combined organic layers were filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (23 mg, 17%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 1.01-1.11, 2.17-2.24, 2.33-2.38, 2.45-2.77, 3.15-3.56, 4.03-4.20, 4.44-4.53, 5.18-5.28, 7.27-7.34, 7.59-7.66. Some signals overlap with solvent. HRMS (M+H)+: calculated 327.0708. found 327.0722.

Provenance & Evidence