3-Chloro-6-hydroxyacetophenone → Kdm1A-IN-29

HRID 1777052노트

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HRID 1777052 반응식
[NH:1]([C:3]([C:5]1[CH:6]=[C:7]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4])[NH2:2].[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([C:23](=O)[CH3:24])[CH:22]=1>CO.C(O)(=O)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([OH:26])=[C:21](/[C:23](=[N:2]/[NH:1][C:3]([C:5]2[CH:6]=[C:7]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)=[O:4])/[CH3:24])[CH:22]=1

참가 물질

5

반응물 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 677513503-(hydrazinecarbonyl)-N-methylbenzenesulfonamide

생성물 1

HCID 136265204Kdm1A-IN-29수율 36.8%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

반응 조건

온도
120 °C

실험 절차

3-(hydrazinecarbonyl)-N-methylbenzenesulfonamide (120 mg, 0.523 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (89 mg, 0.523 mmol) was dissolved in Methanol (Volume: 4 ml) in the presence of acetic acid as a catalyst and then the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. Reaction was monitored by TLC. After completion of the reaction, following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) afforded the title compound (E)-3-(2-(1-(5-chloro-2-hydroxyphenyl)ethylidene)hydrazinecarbonyl)-N-methylbenzenesulfonamide (75 mg, 0.192 mmol, 36.8% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 8.21 (m, 1H), 8.06 (m, 1H), 7.95 (d, 1H, J=7.6 Hz), 7.59 (t, 1H, J=8.0 Hz), 7.39 (d, 1H, J=2.4 Hz), 7.18 (m, 1H), 6.90 (d, 1H, J=8.0 Hz), 2.56 (s, 3H), 2.36 (5, 3H). Mass [M+H]+: 382.1

후처리

  1. customReaction
  2. customAfter completion of the reaction
  3. temperaturefollowing cooling
  4. customthe solvent was removed by vacuum
  5. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

출처 및 근거

ORD 기록
ord-46b632af9d8d4a8c92696f20710853cb
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266838B2

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