(S)-4-{4-[2-(3-cyanopropylidene)hydrazino]benzyl}-1,3-oxazolidin-2-one → 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan Acetonitrile

HRID 1608999Notes

Reaction equation

HRID 1608999 reaction equation
C(CCC=N[NH:7][C:8]1[CH:20]=[CH:19][C:11]([CH2:12][C@H:13]2[CH2:17][O:16][C:15](=[O:18])[NH:14]2)=[CH:10][CH:9]=1)#N>C(Cl)(Cl)Cl>[C:8]([CH2:9][C:10]1[C:9]2[C:8](=[CH:20][CH:19]=[C:11]([CH2:12][C@H:13]3[CH2:17][O:16][C:15](=[O:18])[NH:14]3)[CH:10]=2)[NH:7][CH:11]=1)#[N:7]

Participants

3

Reactant 1

HCID 70196055(S)-4-{4-[2-(3-cyanopropylidene)hydrazino]benzyl}-1,3-oxazolidin-2-one

Product 1

HCID 539136153-Des[2-(Dimethylamino)ethyl] Zolmitriptan AcetonitrileYield 153.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the product from step (b) (2.5 g) and polyphosphate ester (20.0 g) in chloroform (40 ml) was refluxed for 20 minutes. Ice was added to the cooled mixture and the chloroform evaporated in vacuo. The remaining aqueous phase was extracted with ethyl acetate and the combined extracts evaporated in vacuo to give the desired product as a pale yellow oil (1.8 g).

Workup

  1. additionIce was added to the cooled mixture
  2. customthe chloroform evaporated in vacuo
  3. extractionThe remaining aqueous phase was extracted with ethyl acetate
  4. customthe combined extracts evaporated in vacuo

Sources & evidence

ORD record
ord-afeb9de70e514fe1a243dbec184ff51d
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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