Sodium Azide → HCID 178500554, compound

HRID 593212Notes

Reaction equation

HRID 593212 reaction equation
[C:1]([C:3]1[N: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]=[N: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 117748262HCID 117748262, compound

Product 1

HCID 178500554HCID 178500554, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of methyl 4-[(5-cyanopyrazin-2-yl)amino]-4-oxo-butanoate A4 (0.168 g, 0.7173 mmol), sodium azide (0.141 g, 0.076 mL, 2.15 mmol) and triethylammonium chloride (0.156 g, 0.146 mL, 1.11 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 combined organic phases were combinated, dried over sodium sulfate and concentrated. The residue was suspended in ethyl acetate and filtered to methyl 4-oxo-4-[[5-(1H-tetrazol-5-yl)pyrazin-2-yl]amino]butanoate A36 (0.085 g, 43% yield). M.p.: 270-274° C. LC-MS (Method F): RT 0.49, 278 (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 to methyl 4-oxo-4-[[5-(1H-tetrazol-5-yl)pyrazin-2-yl]amino]butanoate A36 (0.085 g, 43% yield)
  6. customRT 0.49, 278 (M+H+)

Sources & evidence

ORD record
ord-ef2b02af72a1489f9a5bfb416ac18537
Source dataset
uspto-grants-2016_01
Patent number
US09241489B2

Reaction notes

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