[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]([OH:16])=O)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:16])=[CH:5][CH:4]=1To a mixture of 4-methoxy-8-methyl-1-naphthoic acid (above Step-5 intermediate) (1 equiv) in dry DMF (8 mL) was added, EDC.HCl (1.4 equiv) and HOBt (1.4 equiv) and the mixture was stirred for 10 min. To this, morpholine (1.5 equiv) and DIPEA (3 equiv) were added and the reaction mixture was stirred overnight. It was quenched with water (20 mL) and the aqueous layer was extracted with EtOAc (4×20 mL). The combined organic layer was washed with water (20 mL), 5% NaHCO3 solution (20 mL), brine (25 mL), dried (Na2SO4) and filtered. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography to furnish the title compound.
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