Triethylamine → 3-(1-methylethyl)-4-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-piperazinyl)methyl)-2-piperazinone

HRID 1972562Notes

Reaction equation

HRID 1972562 reaction equation
[CH3:1][CH:2]([CH:4]1[N:9]([CH2:10][C@H:11]2[CH2:16][NH:15][CH2:14][CH2:13][NH:12]2)[CH2:8][CH2:7][NH:6][C:5]1=[O:17])[CH3:3].C(N(CC)CC)C.[N+:25]([C:28]1[S:32][C:31]([S:33](Cl)(=[O:35])=[O:34])=[CH:30][CH:29]=1)([O-:27])=[O:26]>C(Cl)Cl>[CH3:3][CH:2]([CH:4]1[N:9]([CH2:10][C@H:11]2[CH2:16][N:15]([S:33]([C:31]3[S:32][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=3)(=[O:35])=[O:34])[CH2:14][CH2:13][NH:12]2)[CH2:8][CH2:7][NH:6][C:5]1=[O:17])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 217873475-Nitrothiophene-2-sulfonyl chlorideHCID 665825553-(1-methylethyl)-4-((2R)-2-piperazinylmethyl)-2-piperazinone

Product 1

HCID 665829503-(1-methylethyl)-4-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-piperazinyl)methyl)-2-piperazinoneYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-(1-methylethyl)-4-((2R)-2-piperazinylmethyl)-2-piperazinone (186 mg, 0.774 mmol) and triethylamine (324 μL, 2.32 mmol) in CH2Cl2 (5.00 mL) was added a solution of 5-nitrothiophene-2-sulfonyl chloride (190 mg, 0.836 mmol, Enamine, Kiev, Ukraine) in CH2Cl2 (1 mL) drop-wise at room temperature. The solution was stirred for 30 min and then the mixture was concentrated. The residue was dissolved in CH2Cl2, the organics were washed with water followed by brine. The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was taken up in MeOH and was passed through an AccuBond SPE SCX cartridge eluting with 2M ammonia/MeOH to give 3-(1-methylethyl)-4-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-piperazinyl)methyl)-2-piperazinone (263 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washthe organics were washed with water
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluting with 2M ammonia/MeOH

Sources & evidence

ORD record
ord-6e22711561c54d4687135011c80fcca3
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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