Acetamidine monohydrochloride → HCID 178432533, compound

HRID 2249597Notes

Reaction equation

HRID 2249597 reaction equation
Br.BrCC([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=O.Cl.[C:13]([NH2:16])(=[NH:15])[CH3:14].[CH3:17][C:18](C)([O-])C.[K+]>CO>[CH3:14][C:13]1[NH:15][CH:17]=[C:18]([C:9]2[CH:8]=[N:7][CH:6]=[CH:11][CH:10]=2)[N:16]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 178432533HCID 178432533, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromoacetylpyridine hydrobromide (1.0 g) and acetamidine hydrochloride (0.505 g) were suspended in methanol. Potassium tert-butoxide (1.0 g) was added in one portion—the mixture turned slightly yellow. The resulting suspension was heated to reflux for 6 hours and was then cooled and filtered. Solvent was removed in vacuo and the residue was dissolved in CHCl3 and adsorbed onto silica gel that was charged onto a silica gel column. The column was eluted with CH2Cl2/MeOH/NH4OH 90:10:1 and the fractions containing the desired product were combined and evaporated to give an oil (79 mg).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 6 hours
  3. temperaturewas then cooled
  4. filtrationfiltered
  5. customSolvent was removed in vacuo
  6. dissolutionthe residue was dissolved in CHCl3
  7. additionwas charged onto a silica gel column
  8. washThe column was eluted with CH2Cl2/MeOH/NH4OH 90:10:1
  9. additionthe fractions containing the desired product
  10. customevaporated

Sources & evidence

ORD record
ord-77018b6075be4b0a8ddbe9adc0688063
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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