Sodium Azide → HCID 178500551, compound

HRID 525999Notes

Reaction equation

HRID 525999 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:17])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=1)#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].C([NH+](CC)CC)C>CN1CCCC1=O.O>[O:17]=[C:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]2[NH:20][N:19]=[N:18][N:2]=2)=[CH:8][N:7]=1)[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 71503460HCID 71503460, compound

Product 1

HCID 178500551HCID 178500551, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of methyl 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoate A1 (0.200 g, 0.857 mmol), sodium azide (0.169 g, 0.09 ml, 2.57 mmol) and triethylammonium chloride (0.187 g, 0.17 ml, 1.33 mmol) was stirred 4 h at 150° C. in 1-methyl-2-pyrrolidinone (10 mL). The mixture was cooled down and diluted with water. After acidification with aqueous hydrochloric acid (1N), the filtrate was extracted twice with ethyl acetate. The organic phases were combined, dried over sodium sulfate and concentrated. The residue was suspended in ethyl acetate and filtered to give methyl 4-oxo-4-[[5-(1H-tetrazol-5-yl)-2-pyridyl]amino]butanoate A65 (0.06 g, 25% yield). M.p.: 246-248° C., LC-MS (Method F) RT 0.53, 277 (M+H+).

Workup

  1. temperatureThe mixture was cooled down
  2. extractionAfter acidification with aqueous hydrochloric acid (1N), the filtrate was extracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0039d5fdab2440eb8f3ccf5ecc9860d7
Source dataset
uspto-grants-2016_05
Patent number
US09345244B2

Reaction notes

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