Ethyl cyanoacetate → 2-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile

HRID 1394169Notes

Reaction equation

HRID 1394169 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH2:10])[CH3:2].[C:11]([CH2:13][C:14](OCC)=O)#[N:12]>>[CH2:1]([N:3]1[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=[C:14]1[CH2:13][C:11]#[N:12])[CH3:2]

Participants

3

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 120363924-N-ethylpyridine-3,4-diamine

Product 1

HCID 468352622-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrileYield 37.3%

Procedure

The product from Step 2 (500 mg, 3.6 mmole) and ethyl cyanoacetate (620 mg, 5.5 mmol) were heated together at 190° C. for 20 minutes. After cooling to room temperature, the residue was purified by column chromatography eluting with 10% methanol in ethyl acetate to afford the title compound (250 mg, 37%); MS (ES+) m/e 187 [M+H]+.

Workup

  1. customthe residue was purified by column chromatography
  2. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-ebcc45573a904d45bc1b6c093e6679a4
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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