Guanidine Hydrochloride → HCID 22260979, compound

HRID 1610109Notes

Reaction equation

HRID 1610109 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].CN(C)/[CH:9]=[CH:10]/[C:11]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][N:14]=1)=O.[Cl-].[NH4+]>C(O)C>[NH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:11]2[CH:10]=[CH:9][N:3]=[C:4]([NH2:6])[N:5]=2)=[N:14]1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 22260629(2E)-3-(Dimethylamino)-1-(1H-indazol-3-yl)-2-propen-1-one

Product 1

HCID 22260979HCID 22260979, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A total of 20 mg of metallic sodium was dissolved in 5 ml of dry ethanol. To the resulting solution were added 76 mg of guanidine hydrochloride and 85 mg of (E)-3-(dimethylamino)-1-(1H-3-indazolyl)-2-propen-1-one, followed by heating under reflux for 12 hours. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=7:5), to give 55 mg of the title compound as a colorless powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 12 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (ethyl acetate:hexane=7:5)

Sources & evidence

ORD record
ord-5b3bc6c905704f6ba4da1fa785ea68a4
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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