Furo[3,4-b]pyridine-5,7-dione → HCID 432832, compound

HRID 897330Notes

Reaction equation

HRID 897330 reaction equation
[N:1]1[C:6]2[C:7](=[O:11])O[C:9](=[O:10])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])#[C-].C1CCN2C(=NCCC2)CC1>CN(C=O)C.C1COCC1>[OH:11][C:7]1[C:6]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:9](=[O:10])[NH:12][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 547815Methyl isocyanoacetate

Product 1

HCID 432832HCID 432832, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

This compound was prepared as described in M. Suzuki et.al., Synthetic Communications, 1978, pg. 461. To a solution of furo[3,4]pyridine-5,7-dione (130 g, 872 mmol) in anhydrous DMF (250 ml) was added 1 liter of dry THF and methyl isocyanoacetate (86.4 g, 872 mmol). This was stirred for 15 minutes at 40° C. under nitrogen, followed by dropwise addition of DBU (132.8 g, 130.4 ml, 872 mmol) which was dissolved in THF (300 ml). After one hour the solvent was removed under reduced pressure and the resultant crude 2-[4-(methoxycarbonyl)-1,3-oxazol-5-yl]nicotinic acid and regioisomeric 3-[4-(methoxycarbonyl)-1,3-oxazol-5-yl]pyridine-2-carboxylic acid products were taken up into MeOH (1 liter). Concentrated HCl (12 M, 291 ml) was then added dropwise while the solution stirred at 55° C. This was stirred for 0.5 hours at which time the crude solids were collected by vacuum filtration. The desired regioisomer was purified by successive recrystallizations in methanol. This provided pure yellow solids. TLC (silica, 90:10:3, dichloromethane, methanol, acetic acid), R f (desired regioisomer)=0.23, R f (undesired regioisomer)=0.62.

Workup

  1. customThis compound was prepared
  2. customAfter one hour the solvent was removed under reduced pressure
  3. additionConcentrated HCl (12 M, 291 ml) was then added dropwise while the solution
  4. stirringstirred at 55° C
  5. stirringThis was stirred for 0.5 hours at which time the crude solids
  6. filtrationwere collected by vacuum filtration
  7. customThe desired regioisomer was purified by successive recrystallizations in methanol

Sources & evidence

ORD record
ord-6ad10ed40c5a4c428a149976897f77f2
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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