Diisopropylethylamine → 3-(6-Phenyl-2-benzothiazolyl)cyclopentanamine

Participants

Reaction Steps

To a suspension of (1R,3R)-3-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (35.7 mg, 0.156 mmol) in DMF (1 mL) was added DIPEA (0.082 mL, 0.47 mmol), 3-((4-methoxybenzyl)thio)-[1,1′-biphenyl]-4-amine (50 mg, 0.16 mmol) and HATU (89 mg, 0.23 mmol). The reaction was stirred rt for 16 h. The mixture was concentrated, and the residue was dissolved in DCM and washed with 1 N HCl and water. The organics were combined and dried over Na2SO4 and concentrated. TFA (1 mL) was added to the residue and the solution was heated at 100° C. for 15 min in microwave. The reaction was heated at 60° C. for 16 h. The reaction was concentrated and dissolved in ACN and purified by Prep HPLC (5-90% B over 12 min, Column: PHENOMENEX® Luna Axia 5 u C18 30×100 mm; Solvent A: 10% ACN−90% H2O-0.1% TFA; Solvent B: 90% ACN−10% H2O-0.1% TFA, flow rate=40 mL/min) to give Intermediate 47 (22 mg, 48%) as a white solid. LC-MS (ESI) 295.0 (M+H), RT=1.86 min (Method B).

Provenance & Evidence