Triphenylphosphine → HCID 22498670, compound

HRID 1814764Notes

Reaction equation

HRID 1814764 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:16])[C:8]2[CH:15]=[CH:14][CH:13]=[N:12][C:9]=2[NH:10][N:11]=1)=[O:5])C.C(OC(=O)C(=[N+]=[N-])C(C1C(Cl)=NC=CC=1)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OC(C)C)(C)C>[O:16]=[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[N:11][NH:10][C:9]2[N:12]=[CH:13][CH:14]=[CH:15][C:8]1=2

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86759634HCID 86759634, compound

Product 1

HCID 22498670HCID 22498670, compoundYield 158.3%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

4-Oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylic acid ethyl ester—3-(2-Chloropyridin-3-yl)-2-diazo-3-oxopropionic acid ethyl ester (5 g) in diisopropyl ether (150 ml) was treated with triphenylphosphine (5.7 g) and stirred at ambient temperature for 18 hours. The resulting solid was filtered off and dried in vacuo then treated with methanol (250 ml) and water (50 ml) and heated under reflux for 2 hours. The methanol was distilled off and the resulting aqueous extracted with EtOAc. The organic was dried and evaporated. Chromatography (EtOAc/hexane) gave title compound (3.2 g). MS (−ve ion chemical ionisation) m/z 218 ([M−H]−, 100%).

Workup

  1. filtrationThe resulting solid was filtered off
  2. customdried in vacuo
  3. additionthen treated with methanol (250 ml) and water (50 ml)
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. distillationThe methanol was distilled off
  7. extractionthe resulting aqueous extracted with EtOAc
  8. customThe organic was dried
  9. customevaporated

Sources & evidence

ORD record
ord-274b112fc817492aab89e20841402017
Source dataset
uspto-grants-2005_04
Patent number
US06878704B2

Reaction notes

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