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

HRID 1844508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844508
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

Komponenten

6

Edukt 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

Produkt 1

HCID 71477483(S)-N-((3-(3-fluoro-4-(5-(pyridin-3-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamideAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3b86b962a3004b50a9d7546a07e1cb48
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946436B2

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