HCID 10332165, compound → HCID 22416536, compound
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][CH:27]([CH3:29])[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][CH:27]([CH3:29])[CH3:28])[CH:25]=1)=[N:8][CH2:7][CH2:6][O:2][N+:3]([O-:5])=[O:4])#[N:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-nitroxyethylamine hydrochloride (95 mg, 0.67 mmol) in DMF (1 ml) was added sodium methoxide (25 mg, 0.46 mmol) followed by a solution of propyl N-cyano-5-isopropylamino-3-pyridinecarboximidate (80 mg, 0.33 mmol) described in Example 11 of Experimental Example 1 in DMF (1 ml), and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction mixture was concentrated to dryness 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 (26 mg, yield 27%) as colorless crystals.
Workup
- concentrationthe reaction mixture was concentrated to dryness under reduced pressure
- extractionextracted with chloroform
- dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue thus obtained
- customwas purified by silica gel column chromatography with a mixed solvent of methanol and chloroform as an eluent
Sources & evidence
- ORD record
- ord-48797bf6a3764f1aae01da8d1e93a652
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05508293
Reaction notes
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