Tetrahydrofuran → 4-(2-Tert-butyl-4-nitrothiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one

HRID 18922Notes

Reaction equation

HRID 18922 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[CH3:21][N:22]([CH3:34])[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][NH:28][C:27]([CH3:32])([CH3:31])[C:26]1=[O:33].CCN(C(C)C)C(C)C>S(Cl)(Cl)=O.C(OCC)(=O)C>[C:1]([C:5]1[S:9][C:8]([C:10]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][N:22]([CH3:21])[CH3:34])[C:26](=[O:33])[C:27]2([CH3:32])[CH3:31])=[O:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 586792031-(2-(Dimethylamino)ethyl)-3,3-dimethylpiperazin-2-oneHCID 586792065-Tert-butyl-3-nitrothiophene-2-carboxylic acid

Product 1

HCID 586792244-(2-Tert-butyl-4-nitrothiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-oneYield 85%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A stirred solution of 5-tert-butyl-3-nitrothiophene-2-carboxylic acid (0.214 g, 0.933 mmol) in 2 ml thionyl chloride was warmed at 45° C. for 1 h and then concentrated under vacuum. The residue was dissolved in 2 ml THF and added to a 3 ml THF solution of 1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one (0.242 g, 1.21 mmol) and DIEA (0.362 g, 2.80 mmol). The resulting mixture was stirred at room temperature for 5 minutes, diluted with ethyl acetate, washed with 1N HCl, water, brine, dried and the solvent eliminated under vacuum to yield 0.300 g, (˜85% purity) of 4-(2-tert-butyl-4-nitrothiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethyl-piperazin-2-one that was used as-is for the next step.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in 2 ml THF
  3. washwashed with 1N HCl, water, brine
  4. customdried

Sources & evidence

ORD record
ord-2ebc823aa2a444a6b9c4d7143702c9ef
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

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