Ethyl cyanoacetate → HCID 20076766, compound

HRID 1654751Notes

Reaction equation

HRID 1654751 reaction equation
[N-]1C=CN=C1.[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:33])=[C:16]([N:20]4[CH2:24][CH2:23][CH:22]([NH:25]C(OC(C)(C)C)=O)[CH2:21]4)[C:17]=3[Cl:19])[C:12](=[O:34])[C:11]([C:35]([OH:37])=O)=[CH:10]2)[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[C:44]([CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])#[N:45]>C(#N)C>[ClH:19].[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:33])=[C:16]([N:20]4[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21]4)[C:17]=3[Cl:19])[C:12](=[O:34])[C:11]([C:35](=[O:37])[CH:46]([C:44]#[N:45])[C:47]([O:49][CH2:50][CH3:51])=[O:48])=[CH:10]2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 86748637HCID 86748637, compound

Product 1

HCID 20076766HCID 20076766, compoundYield 140.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.2 g of 1-cyclopropyl-6-fluoro-8-chloro-7-(3-t-butoxycarbonylaminopyrrolidin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid imidazolide and 6.9 g of potassium carbonate were put into 200 ml of acetonitrile, and 5.66 g of ethyl cyanoacetate was added thereto, and then refluxed under heating for 5 hours. Acetonitrile was distilled off under reduced pressure, and then water and ethyl acetate were added thereto. The pH of the reaction mixture was adjusted to about 3 with 1N-HCl, and then the organic layer was separated. The organic layer was dehydrated with anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was purified on a silica gel column chromatography, and 50 ml of 10% HCl-ethyl acetate was added to the purified compound. The reaction mixture was stirred for 30 minutes, and the resulting solid was filtered, and then dried to obtain 3.4 g of the object compound

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperatureunder heating for 5 hours
  4. distillationAcetonitrile was distilled off under reduced pressure
  5. additionwater and ethyl acetate were added
  6. customthe organic layer was separated
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified on a silica gel column chromatography, and 50 ml of 10% HCl-ethyl acetate
  9. additionwas added to the purified compound
  10. filtrationthe resulting solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-54c0fb6ef5b942b191dd5519299b3e93
Source dataset
uspto-grants-1995_04
Patent number
US05409933

Reaction notes

Loading…