Furo[3,4-b]pyridine-5,7-dione → HCID 15052019, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[C:4]([Cl:17])[CH:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:24]([O:26][C:27](=[O:28])[C:19]=12)=[O:25]>O1CCCC1>[Cl:17][C:4]1[CH:3]=[C:2]([NH:1][C:27]([C:19]2[C:20]([C:24]([OH:26])=[O:25])=[CH:21][CH:22]=[CH:23][N:18]=2)=[O:28])[CH:7]=[CH:6][C:5]=1[CH2:8][N:9]1[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[CH2:11][O:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound was prepared in a manner analogous to that of Example 1, Step C, using 4.0 grams (0.016 mole) of 2-[(4-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone and 2.3 grams (0.016 mole) of 2,3-pyridinedicarboxylic anhydride in 175 mL of tetrahydrofuran. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to a residual oil. The oil was crystallized by dissolving it in ethanol and adding diethyl ether until precipitation occurred. The solid was recrystallized in the same manner to yield 2.2 grams of 2-[[2-chloro-4-[(3-carboxy-2-pyridinyl)carbonylamino]phenyl]methyl]-4,4-dimethyl-3-isoxazolidinone; m.p. 94°-96° C.