Benzamidine → HCID 178420139, compound

HRID 538400Notes

Reaction equation

HRID 538400 reaction equation
[C:1]([NH2:9])(=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[CH3:15][N:16]([CH:18]=O)C>>[C:2]1([C:1]2[NH:8][CH:4]=[C:3]([C:2]3[CH:7]=[CH:18][N:16]=[CH:15][CH:1]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 2332BenzamidineHCID 6228DimethylformamideHCID 516892Sodium Bicarbonate

Product 1

HCID 178420139HCID 178420139, compoundYield 72%

Procedure

2-Bromo-1-(pyrindin-4-yl)ethanone hydrobromide (6.4 g, 23 mmol) was added portionwise to a solution of benzamidine (11.2 g, 93 mmol) in dry DMF (50 mL) at 0° C., maintaining an internal temperature of <5° C. The stirred reaction was allowed to warm to rt over 2 h and then heated to 40° C. for 16 h. The crude reaction was poured into saturated aqueous NaHCO3 solution (600 mL), and partition and extracted with EtOAc (3×300 mL). The combined organic layers were dried (Na2SO4) and evaporated. The resulting crude residue was purified by flash chromatography (SiO2, 100:0-90:10 DCM-MeOH) to give 3.68 g (72%) of 4-(2-phenyl-1H-imidazol-4-yl)pyridine: 1H NMR (CDCl3) δ 9.73 (broad s, 1H), 8.61 (d, J=6.0, 1.2 Hz, 2H), 7.91 (d, J=8.0, 1.6 Hz, 2H), 7.77 (d, J=6.0, 1.2 Hz, 2H), 7.57 (s, 1H), 7.48 (m, 3H).

Workup

  1. temperaturemaintaining an internal temperature of <5° C
  2. customThe stirred reaction
  3. temperatureheated to 40° C. for 16 h
  4. customThe crude reaction
  5. custompartition
  6. extractionextracted with EtOAc (3×300 mL)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. customevaporated
  9. customThe resulting crude residue was purified by flash chromatography (SiO2, 100:0-90:10 DCM-MeOH)

Sources & evidence

ORD record
ord-1c538f6dd9654cb59ff44add4d95b061
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

Loading…