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

HRID 128988Notes

Reaction equation

HRID 128988 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-e59a0d1810db42c993454408873e22ae
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

Loading…