Furan → HCID 22396537, compound

HRID 1070382

Reaction equation

HRID 1070382 reaction equation
[CH:1]12[O:10][CH:7]([CH2:8][CH2:9]1)[CH:6]1[CH:2]2[C:3](=[O:12])[NH:4][C:5]1=[O:11].C1(=O)[NH:17][C:16](=O)[CH:15]=C1.O1C=CC=C1.BrCC#N>CC(C)=O.CN(C=O)C>[O:12]=[C:3]1[N:4]([CH2:15][C:16]#[N:17])[C:5](=[O:11])[CH:6]2[CH:2]1[CH:1]1[O:10][CH:7]2[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 8029FuranHCID 10935MaleimideHCID 11534BromoacetonitrileHCID 23972710-Oxa-4-azatricyclo(5.2.1.02,6)decane-3,5-dione

Product 1

HCID 22396537HCID 22396537, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Synthesis took place in analogy to Example VI a from 10-oxa-4-azatricyclo[5.2.1.02,6]decane-3,5-dione (obtainable from maleimide and furan from Diels-Alder reaction for example as described by Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T.; J Org Chem 1997, 62, 4088-4096 and subsequent hydrogenation as described by Ansell, M. F.; Caton, M. P. L.; North, P. C.; Tetrahedron Lett. 1982, 23, 2811) and bromoacetonitrile with the exception that acetone was used as solvent in place of DMF. The substance was employed as crude product in the next reaction.

Workup

  1. customSynthesis
  2. customfrom Diels-Alder reaction for example
  3. customThe substance was employed as crude product in the next reaction

Sources & evidence

ORD record
ord-5397b9d01bdc473a8cd5f7b98554a071
Source dataset
uspto-grants-2005_06
Patent number
US06903089B1

Linked notes

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