Diethyl (ethoxymethylene)malonate → HCID 178469873, compound

HRID 57792Notes

Reaction equation

HRID 57792 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([NH2:11])[NH:9][N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:12]([O:14][C:15](=[O:26])[C:16](=[CH:22]OCC)[C:17](OCC)=[O:18])[CH3:13]>C(O)(=O)C>[CH2:12]([O:14][C:15]([C:16]1[C:17](=[O:18])[N:9]2[N:10]=[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:7]=[C:8]2[NH:11][CH:22]=1)=[O:26])[CH3:13]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 178507271HCID 178507271, compound

Product 1

HCID 178469873HCID 178469873, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-cyclopentyl-2H-pyrazol-3-ylamine (510 mg, 3.4 mmol, 1 eq) in acetic acid (4.8 mL) was added 2-ethoxymethylene-malonic acid diethyl ester (750 μL, 3.7 mmol, 1.1 eq). The mixture was heated at 120° C. for 3 h in a sealed tube. After cooling, the precipitate was filtered and washed with ethanol and diethyl ether and recrystallised from methanol to afford the expected compound as white powder (657 mg, 71% yield).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washwashed with ethanol and diethyl ether
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-8919164089b04b8f88f62bf8a4359138
Source dataset
uspto-grants-2016_09
Patent number
US09434745B2

Reaction notes

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