HCID 367509, compound → HCID 136133147, compound

HRID 2200931Notes

Reaction equation

HRID 2200931 reaction equation
O.[NH2:2][C:3]1[NH:7][N:6]=[N:5][N:4]=1.[C:8]([C:10]1[CH:25]=[CH:24][C:13]([CH:14]=[C:15]([C:21](=O)[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1)#[N:9].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:8]([C:10]1[CH:25]=[CH:24][C:13]([CH:14]2[N:4]3[N:5]=[N:6][N:7]=[C:3]3[NH:2][C:21]([CH3:22])=[C:15]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1)#[N:9]

Participants

5

Reactant 3

HCID 367509HCID 367509, compoundHCID 516892Sodium BicarbonateHCID 178509300HCID 178509300, compound

Product 1

HCID 136133147HCID 136133147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Under an atmosphere of argon, 5-amino-1,2,3,4-tetrazole hydrate (1.0 g, 9.7 mmol) and ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (2.6 g, 10.7 mmol, 1.1 eq.) were dissolved in DMF (50 ml), and solid sodium bicarbonate (4.1 g, 48.5 mmol, 5 eq.) was added. The mixture was stirred at 55° C. for 12 h. The mixture was then filtered and the DMF from the filtrate was distilled off under reduced pressure. The residue was suspended in ethanol and stirred overnight. The product was filtered off and dried under high vacuum. This gave 950 mg (32% of theory) of the title compound.

Workup

  1. filtrationThe mixture was then filtered
  2. distillationthe DMF from the filtrate was distilled off under reduced pressure
  3. stirringstirred overnight
  4. filtrationThe product was filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-aef0ce88716e4f8182f08d80ada10209
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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