Ethyl cyanoacetate → HCID 86685846, compound

HRID 1629756Notes

Reaction equation

HRID 1629756 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([CH3:18])=O)=[CH:14][CH:15]=1.C(O[C:22](=[O:26])[CH2:23][C:24]#[N:25])C.[C:27]([O-])(=O)C.[NH4+:31]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1([C:3]2[CH:27]=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:31][C:22](=[O:26])[C:23]([C:24]#[N:25])=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH3:9])=[CH:15][CH:14]=2)[CH2:18]1

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 80512-HeptanoneHCID 8500p-METHYLACETOPHENONEHCID 517165Ammonium Acetate

Product 1

HCID 86685846HCID 86685846, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of heptan-2-one (51 mg, 0.45 mmol), 1-p-tolylethanone (60 mg, 0.45 mmol), ethyl-2-cyanoacetate (51 mg, 0.45 mmol) and ammonium acetate (42 mg, 0.55 mmol) in anhydrous DMF (0.6 mL) was heated with stirring at 100° C. for 16 h. The reaction was diluted with EtOAc and washed with water. The solvent was removed in vacuo and the product was purified by preparative HPLC (MeOH/H2O/TFA) to provide the desired product (8 mg, 6%) as a white solid. LCMS Anal. Calc'd for C19H24N2O 297.41, found [M+H] 297.2. 1H NMR (500 MHz, CDCl3) δ 0.89 (t, J=6.87 Hz, 3H), 1.24-1.40 (m, 9H), 1.51-1.71 (m, 2H) 2.42 (s, 3H), 2.73-2.97 (m, 2H), 6.09 (s, 1H), 7.30 (d, J=7.70 Hz, 2H), 7.52 (d, J=7.70 Hz, 2H).

Workup

  1. washwashed with water
  2. customThe solvent was removed in vacuo
  3. customthe product was purified by preparative HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-740b7ee54ade4ff797d93c5c2047a1a3
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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