Ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate → Ethyl 4-oxo-2-{[4-(2,2,2-trifluoroethyl)piperazinyl]amino}-4,5-dihydrofuran-3-carboxylate

HRID 402739Notes

Reaction equation

HRID 402739 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([NH2:10])[CH2:6][CH2:5]1.C(O[C:16]1[O:17][CH2:18][C:19](=[O:26])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>C(O)C>[O:26]=[C:19]1[CH2:18][O:17][C:16]([NH:10][N:7]2[CH2:8][CH2:9][N:4]([CH2:3][C:2]([F:1])([F:11])[F:12])[CH2:5][CH2:6]2)=[C:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 13791062Ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylateHCID 800357434-(2,2,2-Trifluoroethyl)piperazin-1-amine

Product 1

HCID 86708414Ethyl 4-oxo-2-{[4-(2,2,2-trifluoroethyl)piperazinyl]amino}-4,5-dihydrofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2,2,2-trifluoroethyl)piperazine-1-amine (4.72 g, 25.8 mmol) in ethanol (43 mL), ethyl 2-ethoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (4.70 g, 23.5 mmol) which similarly prepared according to the procedure described in the Example 74, Third step was added at ambient temperature. The mixture was stirred for 2 h. The precipitate was collected by filtration, washed with diethyl ether and hexane then dried to afford ethyl 4-oxo-2-{[4-(2,2,2-trifluoroethyl)piperazinyl]amino}-4,5-dihydrofuran-3-carboxylate as solid (5.64 g, y. 71%).

Workup

  1. additionwas added at ambient temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with diethyl ether and hexane
  4. customthen dried

Sources & evidence

ORD record
ord-4d39176845a5446dbc3da72c37974a13
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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