HCID 10105346, compound → HCID 22416541, compound

HRID 1720924Notes

Reaction equation

HRID 1720924 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][CH:23]=[C:24]([NH:26][CH2:27][CH3:28])[CH:25]=1)OCCC)#[N:13]>CN(C=O)C>[C:12]([NH:14][C:15]([C:20]1[CH:21]=[N:22][CH:23]=[C:24]([NH:26][CH2:27][CH3:28])[CH:25]=1)=[N:8][CH2:7][CH2:6][O:2][N+:3]([O-:5])=[O:4])#[N:13]

Participants

5

Reactant 3

HCID 10105346HCID 10105346, compoundHCID 10942334Sodium MethoxideHCID 18358043HCID 18358043, compound

Product 1

HCID 22416541HCID 22416541, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-nitroxyethylamine hydrochloride (659 mg, 4.62 mmol) in DMF (1 ml) was added sodium methoxide (227 mg, 4.20 mmol) followed by a solution of propyl N-cyano-5-ethylamino-3-pyridinecarboximidate (195 mg, 0.84 mmol) in DMF (1 ml) described in Example 10 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 redeuced 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 (208 mg, yield 89%) 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 redeuced 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-5faaf1a2322b489f93cab096f86c1fac
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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