[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1.C([O-])(O)=O.[Na+].C(O)(C)C.C(Cl)Cl>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:13]1[CH2:12][CH:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:14]1To a solution of tert-butyl 3-(quinolin-2-yl)azetidine-1-carboxylate (2.8 g, 9.8 mmol, as prepared above) in DCM (10 mL), TFA (10 mL) was added. The resulting mixture was stirred at rt for 2 h and concentrated to obtain a viscous oil which was dried under reduced pressure. The residue obtained was dissolved in DCM (50 mL) and stirred with saturated NaHCO3 (50 mL). The DCM layer was separated and the aqueous layer was concentrated. To the residue obtained, 20% iso-PrOH/DCM (50 mL) was added and stirred for 10 min and filtered. This procedure was repeated three times. The combined filtrates were dried over Na2SO4, filtered, and concentrated to obtain compound 24d as a gummy solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.34 (d, J=8.6 Hz, 1H), 7.94-8.01 (m, 2H), 7.76 (s, 1H), 7.59 (d, J=6.7 Hz, 1H), 7.53 (d, J=8.6 Hz, 1H), 3.89-4.30 (m, 4H), 3.72-3.82 (m, 1H).
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