HCID 86652390, compound → HCID 178476709, compound

HRID 556733Notes

Reaction equation

HRID 556733 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][CH:17]=[O:18])([O-:3])=[O:2].C(=O)(O)[OH:20].[NH2:23][NH:24][C:25]([NH2:27])=[NH:26]>C1COCC1>[C:17]([O-:18])(=[O:20])[CH3:16].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16][CH:17]=[N:23][NH:24][C:25]([NH2:27])=[NH2+:26])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 86652390HCID 86652390, compoundHCID 178513185HCID 178513185, compound

Product 1

HCID 178476709HCID 178476709, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g (8.3 mmol) 4a and 1.1 eqv. of aminoguanidine bicarbonate was mixed in THF and refluxed for 30 min. The solvent was evaporated and the residue was diluted with acetonitrile and the product crystallised. Purification by recrystallisation from acetonitrile yielded 1.35 g (55%) of the final product 5a (m.p. 192-194° C.).

Workup

  1. temperaturerefluxed for 30 min
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with acetonitrile
  4. customthe product crystallised
  5. customPurification
  6. customby recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-ad9161cddaa149189ecdf649df4257e4
Source dataset
uspto-grants-2011_11
Patent number
US08058306B2

Reaction notes

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