IRE1|A kinase-IN-9 → 4-(7-Hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-N-(2-morpholinoethyl)benzamide
Reaction equation
C([C:3]1[C:4]([OH:32])=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C:10](=[O:13])[C:9]([C:14]1[CH:30]=[CH:29][C:17]([C:18]([NH:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:19])=[CH:16][CH:15]=1)=[C:8]2[CH3:31])=O.OC1C=CC2N=C(C3C=CC(C(N4CCN(C)CC4)=O)=CC=3)C=CC=2C=1C=O>CS(O)(=O)=O>[OH:32][C:4]1[CH:3]=[C:12]2[C:7]([C:8]([CH3:31])=[C:9]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[O:19])=[CH:29][CH:30]=3)[C:10](=[O:13])[O:11]2)=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 4 (5 g, 21.2 mmol) and compound 5 (5.6 g, 24.3 mmol) were stirred at 0° C. CH3SO3H (50 mL) was added dropwise. Then the mixture was stirred at RT for 16 h. The reaction mixture was poured into crush ice, extracted by DCM. The DCM layer was washed with sat.Na2HPO4, dried over Na2SO4, filtered, concentrated. The residue was purified by silica gel column (DCM:EtOH=50:1), afforded compound 6 (1.2 g, 18%) as light yellow solid.