Pyridine → HCID 69373917, compound

HRID 1179315Notes

Reaction equation

HRID 1179315 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1.N1C=CC=CC=1.[CH2:21]([O:28][C:29](ON1C(=O)CCC1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[CH2:21]([O:28][C:29]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]([C:11]([O:13][CH3:14])=[O:12])=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 83172Benzyl succinimido carbonateHCID 69374599HCID 69374599, compound

Product 1

HCID 69373917HCID 69373917, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of methyl 3-[(2-aminoethyl)amino]pyridine-2-carboxylate (3.9 g, 18.6 mmol) in CHCl3 (25 mL) was treated with pyridine (3 mL, 37.3 mmol) then 1-{[(benzyloxy)carbonyl]oxy}pyrrolidine-2,5-dione (Aldrich, 5.57 g, 22.3 mmol) for ½ hr. The reaction was quenched with water and extracted three times with CHCl3. The organic layer was dried with Na2SO4, filtered and evaporated to give an oil. The crude was purified on silical gel using an ISCO normal phase system and eluting with a gradient of 50% to 90% EtOAc Hexanes. The clean fractions were combined to give the product as an oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted three times with CHCl3
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThe crude was purified on silical gel
  8. washeluting with a gradient of 50% to 90% EtOAc Hexanes

Sources & evidence

ORD record
ord-d5a109531d964ad9a82df70527f1e67d
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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