Hydrochloric Acid → (S)-N-((3-(3-fluoro-4-(5-(pyridin-3-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

HRID 1844508노트

반응식

HRID 1844508 반응식
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[F:14][C:15]1[CH:16]=[C:17]([N:23]2[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]2=[O:33])[CH:18]=[CH:19][C:20]=1[NH:21]N.C(O)C.Cl>O>[F:14][C:15]1[CH:16]=[C:17]([N:23]2[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]2=[O:33])[CH:18]=[CH:19][C:20]=1[N:21]1[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=[N:2]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 53691653-Dimethylamino-1-(3-pyridyl)-2-propen-1-oneHCID 10731576(S)-N-((3-(3-fluoro-4-hydrazinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

생성물 1

HCID 71477483(S)-N-((3-(3-fluoro-4-(5-(pyridin-3-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide수율 42.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (58 mg, 0.327 mmol) and (S)—N-((3-(3-fluoro-4-hydrazinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (94 mg, 0.327 mmol) were combined with a solvent, ethanol (3 mL), and then the mixture was slowly heated to reflux, followed by addition of concentrated hydrochloric acid (40 μL). The reaction mixture was maintained under reflux until completion of the reaction as monitored by TLC. Then, the reaction mixture was poured into water and then was extracted with dichloromethane. The dichloromethane layer was rotary evaporated. The residue was purified with column chromatography to afford 55 mg light yellow solid, with a yield of 40.7%, melting point: 83.7-85.9° C., HPLC: 98.2%.

후처리

  1. temperaturethe mixture was slowly heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was maintained
  4. temperatureunder reflux until completion of the reaction
  5. extractionwas extracted with dichloromethane
  6. customThe residue was purified with column chromatography

출처 및 근거

ORD 기록
ord-3b86b962a3004b50a9d7546a07e1cb48
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946436B2

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