1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 12875025, compound

HRID 847776Notes

Reaction equation

HRID 847776 reaction equation
Cl[CH:2]1[C:6]2=[N:7][C:8]3[N:9]([CH2:21][CH3:22])[CH:10]=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[O:4][CH2:3]1.C1CCN2C(=NCCC2)CC1>CN(C)C=O>[CH2:21]([N:9]1[C:8]2[N:7]=[C:6]3[CH:2]=[CH:3][O:4][C:5]3=[CH:14][C:13]=2[C:12](=[O:15])[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10]1)[CH3:22]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12788721HCID 12788721, compound2×

Product 1

HCID 12875025HCID 12875025, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.2 g of ethyl 3-chloro-5-ethyl-8-oxo-2,3,5,8-tetrahydrofuro[3,2-b]-1,8-naphthyridine-7-carboxylate (Compound XII where R1 =R3 =C2H5, X=Cl) dissolved in 50 ml of dimethylformamide, 3.2 g of 1,8-diazabicyclo[5,4,0]-7-undecene was slowly added dropwise and the mixture was stirred at 40° to 45° C. for 1 hour. After removal of the solvent, the residue was dissolved in dilute hydrochloric acid and extracted with chloroform. The chloroform layer separated out was washed with water, dried and evaporated in vacuo to obtain 2.3 g of ethyl 5,8-dihydro-5-ethyl-8-oxofuro[3,2-b]-1,8-naphthyridine-7-carboxylate.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in dilute hydrochloric acid
  3. extractionextracted with chloroform
  4. customThe chloroform layer separated out
  5. washwas washed with water
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9261aa12430843d689071065b18865ed
Source dataset
uspto-grants-1981_10
Patent number
US04293695

Reaction notes

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