Piperazin-2-one → HCID 54682864, compound

HRID 2114816Notes

Reaction equation

HRID 2114816 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10](OS(C(F)(F)F)(=O)=O)=[C:9]([C:21]([O:23]CC)=O)[C:8]2=[O:26])=[CH:4][CH:3]=1.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][C:30]1=[O:35]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10]3[N:32]4[CH2:33][CH2:34][NH:29][C:30](=[O:35])[C:31]4=[C:21]([OH:23])[C:9]=3[C:8]2=[O:26])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 58857945HCID 58857945, compound

Product 1

HCID 54682864HCID 54682864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 1-(4-fluorobenzyl)-2-oxo-4-{[(trifluoromethyl)-sulfonyl]oxy}-1,2,5,6-tetrahydropyridine-3-carboxylate (0.67 g, 1.58 mmol) and piperazin-2-one (0.63 g, 6.3 mmol) was heated in a sealed tube at 180° C. in a microwave reactor for 10 minutes with stirring. The resultant solution was diluted with methanol and was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided a semi-purified sample of title compound. Further purification of the product was achieved through formation of the corresponding tosylate. To a solution of the semipurified product (0.1 g, 0.30 mmol) and triethylamine (63 μL, 0.46 mmol) in dichloromethane (2 mL) at room temperature, toluenesulfonyl chloride (58 mg, 0.30 mmol) was added. The resultant solution was stirred at room temperature for two hours. The product was isolated and purified. A solution of the resultant tosylate (30 mg, 0.06 mmol) and sodium methoxide (10 mg, 0.18 mmol) in anhydrous methanol (0.5 mL) was heated at 60° C. for 1 hour. The resultant solution was concentrated under vacuum. The residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. customwas subjected to HPLC purification on C-18 stationary phase
  2. washeluted with water/acetonitrile/TFA mobile phase
  3. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-2c14ce6c2d664a079e554a23d3765c0c
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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