HCID 13565859, compound → HCID 13823371, compound

HRID 868128Notes

Reaction equation

HRID 868128 reaction equation
[F:1][B-](F)(F)F.[CH2:6]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([N+]#N)=[CH:21][CH:20]=[C:19]([N:25]([C:29](=[O:31])[CH3:30])[CH:26]3[CH2:28][CH2:27]3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])[CH3:7]>C1(C)C=CC=CC=1>[C:29]([N:25]([CH:26]1[CH2:28][CH2:27]1)[C:19]1[N:18]=[C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH2:12][CH2:13]2)[C:22]([F:1])=[CH:21][CH:20]=1)(=[O:31])[CH3:30]

Participants

3

Reactant 1

HCID 13565859HCID 13565859, compound

Product 1

HCID 13823371HCID 13823371, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 800 ml of refluxing toluene was added in portions, as a solid, 46.2 g (0.1 mole) of 2-[4-(ethoxycarbonyl)-1-piperazinyl]-6-(acetylcyclopropylamino)-3-pyridinediazonium tetrafluoroborate. After the addition was complete, the reaction was refluxed for ten minutes and the toluene was decanted from the insoluble precipitate. The toluene was evaporated in vacuo and the residue was partitioned between chloroform and water. The chloroform layer was washed with 5% aqueous sodium bicarbonate, water, dried over magnesium sulfate and evaporated in vacuo to give 13.7 g of the title compound, as a viscous oil. An additional 10.2 g could be obtained by partitioning the original toluene insoluble material in chloroform and water. The organic layer was washed with 5% aqueous sodium bicarbonate, dried over magnesium sulfate, evaporated in vacuo and the residue was chromatographed on silica gel eluting with chloroform/ethyl acetate (6:4). This fraction was also a viscous oil which did not crystallize upon standing. Both fractions were of sufficient purity to be used as is in the ensuing steps.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was refluxed for ten minutes
  3. customthe toluene was decanted from the insoluble precipitate
  4. customThe toluene was evaporated in vacuo
  5. customthe residue was partitioned between chloroform and water
  6. washThe chloroform layer was washed with 5% aqueous sodium bicarbonate, water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5c9fe7d6b86040468eec3d6e946b484e
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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