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

HRID 1844507Notes

Reaction equation

HRID 1844507 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])[CH:5]=[CH:6][C:7]=1[NH:8][NH2:9].[CH:21]1[C:26]([CH:27]([CH:30]=O)[CH:28]=O)=[CH:25][CH:24]=[N:23][CH:22]=1>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:30]=[C:27]([C:26]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[CH:28]=[N:9]1

Participants

4

Reactant 2

HCID 27372462-(Pyridin-4-yl)malonaldehydeHCID 10731576(S)-N-((3-(3-fluoro-4-hydrazinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Product 1

HCID 71477480(S)-N-((3-(3-fluoro-4-(4-(pyridin-4-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamideYield 66.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 mg (0.354 mmol) of (S)—N-{[3-(3-fluoro-4-hydrazinophenyl)-2-oxooxazolidin-5-yl]methyl}-acetamide and 52.8 mg (0.354 mmol) of 2-(4-pyridyl)malondialdehyde were combined with 5 mL ethanol as a solvent. Then, the resultant mixture was slowly heated to reflux, thereby the solid was substantially dissolved. TLC monitoring was performed to determine completion of the reaction. Then, the resultant mixture was cooled to room temperature and vacuum filtered to afford the product (13a) as a light yellow solid, with a yield of 66.3%, melting point: 203.8-205.0° C., HPLC: 99.97%.

Workup

  1. temperatureto reflux
  2. dissolutionthe solid was substantially dissolved
  3. customcompletion of the reaction
  4. filtrationvacuum filtered

Sources & evidence

ORD record
ord-e84dd3d7177f4e37a0b4eaa0b82da4ba
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

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