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

HRID 1972562노트

반응식

HRID 1972562 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6e22711561c54d4687135011c80fcca3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431563B2

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