Propylenediamine → HCID 178430407, compound

HRID 714336Notes

Reaction equation

HRID 714336 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=1)[C:13](O)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH:21]([NH2:23])[CH3:22].P(Cl)(Cl)(Cl)=O>O1CCOCC1>[CH3:22][CH:21]1[CH2:20][NH:19][C:13]([C:12]2[CH:16]=[CH:17][N:18]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=2)=[N:23]1

Participants

5

Reactant 3

HCID 6567PropylenediamineHCID 24813Phosphorus oxychlorideHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 178430407HCID 178430407, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-benzamidoisonicotinic acid (0.50 g, 2.06 mmol) and 1,2-diaminopropane (0.35 mL, 4.12 mmol) in 1,4-dioxane (20 mL) was added phosphorus oxychloride (0.94 mL, 10.30 mmol) dropwise at ambient temperature under nitrogen atmosphere. The resulting solution was refluxed for 15 hours, cooled to ambient temperature and concentrated in vacuo to dryness. The residue was diluted with saturated aqueous sodium bicarbonate solution (50 mL), extracted with dichloromethane (4×50 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with ethyl acetate followed by 9:1:0.1 ratio of ethyl acetate, methanol and triethyl amine to give N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide as a pale yellow foam (0.17 g, 29%): MS (ES+) m/z 281.5 (M+1).

Workup

  1. temperatureThe resulting solution was refluxed for 15 hours
  2. concentrationconcentrated in vacuo to dryness
  3. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution (50 mL)
  4. extractionextracted with dichloromethane (4×50 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8e5a8c3f69cd4b97892c464c9c675eab
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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