Furo[3,4-b]pyridine-5,7-dione → HCID 15052019, compound

HRID 329563Notes

Reaction equation

HRID 329563 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]1

Participants

4

Reactant 2

HCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 13557219HCID 13557219, compound

Product 1

HCID 15052019HCID 15052019, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 1, Step C
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure to a residual oil
  4. customThe oil was crystallized
  5. dissolutionby dissolving it in ethanol
  6. additionadding diethyl ether
  7. customuntil precipitation
  8. customThe solid was recrystallized in the same manner

Sources & evidence

ORD record
ord-32c4b19286884a1493cff942e4c3c629
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

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