Phenylhydrazine → HCID 59860240, compound

HRID 472089Notes

Reaction equation

HRID 472089 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[N:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]#[C:32][C:33](OCC)=[O:34])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1>C1COCC1>[C:1]1([N:7]2[C:31]([C:28]3[CH:29]=[C:30]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][CH:22]=[C:21]4[C:18]3[CH:17]=[CH:16][N:15]=[CH:20][CH:19]=3)=[CH:32][C:33](=[O:34])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 23665647Potassium tert-butoxideHCID 66782052HCID 66782052, compound

Product 1

HCID 59860240HCID 59860240, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of phenylhydrazine (0.093 ml, 0.95 mmol) in anhydrous THF (4.0 ml) was treated with a 1M solution of potassium tert-butoxide in THF (1.89 ml, 1.89 mmol). The resulting solution was added to a solution of ethyl 3-[4-(4-pyridinyl)-6-quinolinyl]-2-propynoate (0.268 g, 0.95 mmol) in THF (10 ml). The resulting brown solution was stirred at room temperature for 1 hour then at 65° C. for 1 hour. The resulting orange slurry was cooled to room temperature then concentrated under reduced pressure. The resulting residue was taken into saturated aqueous NaHCO3 then extracted into methylene chloride and the extracts were dried over sodium sulfate then evaporated under reduced pressure. The resulting oil was purified by HPLC (acetonitrile/water, 5-80% gradient). The product was concentrated to a residue then recrystallized from ethanol to give the title compound (0.020 g, 6%) as a white solid. MS (ES)+ m/e 365 [M+H]+.

Workup

  1. waitat 65° C. for 1 hour
  2. temperatureThe resulting orange slurry was cooled to room temperature
  3. concentrationthen concentrated under reduced pressure
  4. extractionthen extracted into methylene chloride
  5. dry with materialthe extracts were dried over sodium sulfate
  6. customthen evaporated under reduced pressure
  7. customThe resulting oil was purified by HPLC (acetonitrile/water, 5-80% gradient)
  8. concentrationThe product was concentrated to a residue
  9. customthen recrystallized from ethanol

Sources & evidence

ORD record
ord-dd9df16ef5d446b3af1c7696d33b7b6a
Source dataset
uspto-grants-2014_01
Patent number
US08633187B2

Reaction notes

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