2-Aminopyridine → HCID 86611118, compound

HRID 448429Notes

Reaction equation

HRID 448429 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]1[C:13](=[O:14])[N:12]([O:15][C:16](ON2C(=O)CCC2=O)=[O:17])[C:10](=[O:11])[CH2:9]1>C(#N)C>[O:11]=[C:10]1[CH2:9][CH2:8][C:13](=[O:14])[N:12]1[O:15][C:16](=[O:17])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 676246Di(succinimido) carbonate

Product 1

HCID 86611118HCID 86611118, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-aminopyridine (2.0 g, 21.3 mmol) in acetonitrile (20 mL) was added to a stirred suspension of N,N-disuccinimidyl carbonate (5.4 g, 21.3 mmol) in acetonitrile (150 mL). The mixture was stirred at room temperature overnight. The mixture was concentrated, and the residue was dissolved in methylene chloride (120 mL). The methylene chloride solution was washed with sat. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL) and dried (MgSO4). Solvent was removed, and the residue was slurried with ether (30 mL) to give pyridin-2-yl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl ester (2.5 g).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride (120 mL)
  3. washThe methylene chloride solution was washed with sat. NaHCO3 (40 mL), water (2×40 mL), brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed

Sources & evidence

ORD record
ord-14204324a2e14b40adf821b38dfe1a0c
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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