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

HRID 1844508Notes

Reaction equation

HRID 1844508 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(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%.

Workup

  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

Sources & evidence

ORD record
ord-3b86b962a3004b50a9d7546a07e1cb48
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

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