Formamidine acetate → HCID 25152290, compound

HRID 1159177Notes

Reaction equation

HRID 1159177 reaction equation
[CH2:1]([N:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][CH:5]([NH2:8])[CH2:6][NH2:7])[CH3:2].[C:15](O)(=O)C.C(N)=N>C(O)C>[N:7]1[CH2:6][CH:5]([CH2:4][N:3]([CH2:1][CH3:2])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:8][CH:15]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 68644151HCID 68644151, compound

Product 1

HCID 25152290HCID 25152290, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of rac-N1-ethyl-N1-phenyl-propane-1,2,3-triamine (0.19 g, 1.0 mmol) in ethanol (5 ml) was added formamidine acetate (0.11 g, 1.08 mmol) and the mixture was stirred overnight at room temperature. The solvent was evaporated, water (5 ml) was added and the mixture was extracted 3 times with dichloromethane (10 ml). The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:ethyl acetate/methanol=90:10) to yield an off-white amorphous solid (0.042 g, 21%); MS (ISP): 204.1 ((M+H)+).

Workup

  1. customThe solvent was evaporated
  2. additionwater (5 ml) was added
  3. extractionthe mixture was extracted 3 times with dichloromethane (10 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:ethyl acetate/methanol=90:10)

Sources & evidence

ORD record
ord-d2f2c41b72bd4a19b3dfa81282b84f27
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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