Acrylonitrile → HCID 22562162, compound

HRID 982613

Reaction equation

HRID 982613 reaction equation
FC(F)(F)C([NH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=O.C(N(CC)CC)C.[C:21](#[N:24])[CH:22]=[CH2:23]>C1COCC1>[C:21]([CH2:22][CH2:23][N:9]1[CH2:8][CH2:7][CH:6]([NH2:5])[CH2:11][CH2:10]1)#[N:24]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 107742532,2,2-trifluoro-N-(piperidin-4-yl)acetamide

Product 1

HCID 22562162HCID 22562162, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3 g (15.3 mmol) of 4-trifluoroacetamidopiperidine, 3 g (4.25 mL, 30.6 mmol) of triethylamine, 3 mL (45.9 mmol) of acrylonitrile in 10 mL of THF was stirred at room temperature for 17 hr. The solvent and volatile were evaporated under reduced pressure. The residue was dissolved in 20 mL of methanol and 4 mL of 30% NH4OH and the solution was refluxed for 5 hr. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel eluting first with 500 mL of dichloromethane, then 500 mL of 0.5% methanol/dichloromethane, followed by 1000 mL of 9:1:0.1 dichloromethane/methanol/ammonium hydroxide to give 0.7 g (30% yield) of the N-(2-cyanoethyl)-4-aminopiperidine. Step 4: Preparation of 6-(2-chlorophenyl)-2-(N-2-cyanoethylpiperidyl-4-amino)-pyrido[2,3-d]-pyrimidin-7-ol

Workup

  1. customThe solvent and volatile were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 20 mL of methanol
  3. temperature4 mL of 30% NH4OH and the solution was refluxed for 5 hr
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel eluting first with 500 mL of dichloromethane

Sources & evidence

ORD record
ord-8c3f64fbee9441ae8730b14989629cfd
Source dataset
uspto-grants-2005_03
Patent number
US06861423B2

Linked notes

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