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m-Chloroperbenzoic acid → HCID 71224273、化合物

HRID 2402944
ノート
印刷プレビュー

反応式

HRID 2402944 の反応式
[C:1]([C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11](SC)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=O.CCN(C(C)C)C(C)C.[CH3:42][N:43]1[CH2:48][CH2:47][N:46]([C:49]2[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=2)[CH2:45][CH2:44]1>ClCCl>[C:1]([C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[C:11]([NH:53][C:52]2[CH:51]=[CH:50][C:49]([N:46]3[CH2:45][CH2:44][N:43]([CH3:42])[CH2:48][CH2:47]3)=[CH:55][CH:54]=2)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 71224526HCID 71224526、化合物

生成物 1

HCID 71224273HCID 71224273、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

To a cold (0° C.) solution of Example 3A (200 mg, 0.661 mmol) in dichloromethane (2.2 mL) was added meta-chloroperoxybenzoic acid (179 mg, 0.728 mmol) in a single portion. After 1 hour, the reaction mixture was partitioned between 10% sodium thiosulfate solution and ethyl acetate. The layers were separated, and the organic layer was washed with saturated sodium bicarbonate solution, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (3 mL). Hunig's base (231 μl, 1.323 mmol) and 4-(4-methylpiperazin-1-yl)aniline (127 mg, 0.661 mmol) were added to the solution, and the reaction was heated to 45° C. for 3 hours. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure. The crude residue was purified by MPLC (10 g SiO2), eluting with dichloromethane to 10% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 446.3 [M+H]+.

後処理

  1. customthe reaction mixture was partitioned between 10% sodium thiosulfate solution and ethyl acetate
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated sodium bicarbonate solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in N,N-dimethylformamide (3 mL)
  8. temperatureThe reaction mixture was cooled to room temperature
  9. custompartitioned between water and ethyl acetate
  10. concentrationThe organic layer was concentrated under reduced pressure
  11. customThe crude residue was purified by MPLC (10 g SiO2)
  12. washeluting with dichloromethane to 10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-1d17ba3c6926403ea8630151102915fa
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08796289B2

反応ノート

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