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

HRID 1972562ノート

反応式

HRID 1972562 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6e22711561c54d4687135011c80fcca3
出典データセット
uspto-grants-2013_04
特許番号
US08431563B2

反応ノート

読み込み中…