Ethyl cyanoacetate → HCID 57929844, compound

HRID 1930070Notes

Reaction equation

HRID 1930070 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([CH3:13])[CH3:12])=[N:9][N:10]=2)[N:7]=1.[C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15].[H-].[Na+]>CN(C=O)C>[C:14]([CH:16]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([CH3:13])[CH3:12])=[N:9][N:10]=2)[N:7]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 397324056-Chloro-3-(propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 57929844HCID 57929844, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine (5.00 g, 25.4 mmol, Preparation #G.1) and ethyl 2-cyanoacetate (3.16 g, 28.0 mmol) were added to DMF (50 mL) then the solution was cooled to about 0° C. Sodium hydride (60% in oil, 1.22 g, 30.5 mmol) was added then the mixture was stirred for about 5 min at ambient temperature and at about 60° C. for about 14 h. The mixture was cooled to ambient temperature then concentrated under reduced pressure. The residue was stirred with EtOAc (100 mL) and 2N HCl (50 mL) for about 10 min and the insoluble material was collected by filtration and dried to give the title compound (1.16 g, 17%): LC/MS (Table 1, Method g) Rt=1.53 min; MS m/z: 273.9 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationthen concentrated under reduced pressure
  3. stirringThe residue was stirred with EtOAc (100 mL) and 2N HCl (50 mL) for about 10 min
  4. filtrationthe insoluble material was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-8367d8be721f4467812de8efa79fed04
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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