Ethyl cyanoacetate → HCID 21110161, compound

HRID 639159Notes

Reaction equation

HRID 639159 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([CH3:14])=[CH:11][C:12]#[N:13])[CH:6]=[CH:7][CH:8]=1.[CH:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)=O.[C:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])#[N:28].N1CCCCC1>C(O)C>[NH2:28][C:27]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:16])[F:1])[CH:4]=2)[C:10]([CH3:14])=[C:11]([C:12]#[N:13])[CH:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 50752873-{[3-(Trifluoromethyl)phenyl]amino}but-2-enenitrile

Product 1

HCID 21110161HCID 21110161, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 100 mg (0.44 mmol) of the compound of Example 2A, 57.97 mg (0.44 mmol) 4-formylbenzonitrile and 50.01 mg (0.44 mmol) ethyl cyanoacetate are dissolved in 2 ml ethanol. 3.76 mg (4.4 μl, 0.04 mmol) piperidine are added, and the mixture is stirred at reflux overnight. After cooling down to room temperature, the formed crystals are filtered and washed twice with ethanol. The crude product is purified by column chromatography with cyclohexane/ethyl acetate mixtures as eluent.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe formed crystals are filtered
  3. washwashed twice with ethanol
  4. customThe crude product is purified by column chromatography with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-0364a46c3a01475783ca2d9054f91de2
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

Loading…