Triethylamine → HCID 178469368, compound

HRID 2401176Notes

Reaction equation

HRID 2401176 reaction equation
Cl.[CH:2]([NH2:4])=[NH:3].[C:5](OCC)(=[O:13])[C:6]#[C:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C>C(#N)C>[OH:13][C:5]1[N:4]=[CH:2][N:3]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69803Diethyl acetylenedicarboxylateHCID 10313058Methanimidamide, hydrochloride (1:1)

Product 1

HCID 178469368HCID 178469368, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Formamidine hydrochloride (2.0 g, 45.4 mmol) and diethyl 2-butynedioate (7.23 mL, 45.4 mmol) were added together in acetonitrile (85 mL) and the resulting mixture was treated dropwise with triethylamine (6.33 mL, 45.4 mmol). The resulting mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool to room temperature, further cooled in an ice bath and the resulting solid was collected by filtration and discarded. The filtrate was evaporated under reduced pressure and the residue purified by column chromatography (Biotage SP4) eluting with a gradient of 0-100% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as an off white solid (0.995 g);

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturefurther cooled in an ice bath
  4. filtrationthe resulting solid was collected by filtration
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue purified by column chromatography (Biotage SP4)
  7. washeluting with a gradient of 0-100% ethyl acetate and iso-hexane
  8. additionProduct containing fractions
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-92a82815666640f9bd5a7d737fa74e15
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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