Sodium Methoxide → HCID 22416572, compound

HRID 1720925Notes

Reaction equation

HRID 1720925 reaction equation
Cl.[O:2]([CH2:6][CH2:7][NH2:8])[N+:3]([O-:5])=[O:4].C[O-].[Na+].[C:12]([N:14]=[C:15]([C:20]1[CH:21]=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=1)OCCC)#[N:13]>CN(C=O)C>[NH2:26][C:23]1[N:22]=[CH:21][C:20]([C:15](=[N:8][CH2:7][CH2:6][O:2][N+:3]([O-:5])=[O:4])[NH:14][C:12]#[N:13])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 18358043HCID 18358043, compoundHCID 22416550HCID 22416550, compound

Product 1

HCID 22416572HCID 22416572, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-nitroxyethylamine hydrochloride (1.36 g, 9.54 mmol) in DMF (3.5 ml) was added sodium methoxide (470 mg, 8.7 mmol) followed by a solution of propyl N-cyano-6-amino-3-pyridinecarboximidate (355 mg, 1.74 mmol) in DMF (2 ml) described in Example 5 of Experimental Example 1, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction mixture was evaporated under reduced pressure. The residue was suspended in water and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography with a mixed solvent of methanol and chloroform as an eluent to give the title compound (284 mg, yield 74%) as colorless crystals.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography with a mixed solvent of methanol and chloroform as an eluent

Sources & evidence

ORD record
ord-0032b5f5054e4bf49dd1a2224f829a3b
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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