Water → HCID 178464833, compound

HRID 448823Notes

Reaction equation

HRID 448823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:15][C:14](=[O:16])[NH:13][NH:12]2)=[O:10])=[C:4]([C:17](=[O:24])[NH:18][CH:19]([CH:21]2[CH2:23][CH2:22]2)[CH3:20])[CH:3]=1.Cl[C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][N:27]=1.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[N:12]([C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][N:27]=3)[N:13]=[C:14]([OH:16])[CH2:15]2)=[O:10])=[C:4]([C:17](=[O:24])[NH:18][CH:19]([CH:21]2[CH2:22][CH2:23]2)[CH3:20])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 169882,3-DichloropyridineHCID 24758Sodium hydrideHCID 44185604N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-5-oxopyrazolidine-3-carboxamide

Product 1

HCID 178464833HCID 178464833, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

1.0 g of N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-5-oxopyrazolidine-3-carboxamide was dissolved in 10 mL of N,N-dimethylformamide, and 460 mg of 2,3-dichloropyridine and then 350 mg of sodium hydride were added, followed by stirring at about 70° C. for about 7 hours in a nitrogen atmosphere, and then the reaction liquid was left to cool. To the reaction liquid, water and ethyl acetate were added, followed by stirring and extraction with ethyl acetate. Then, concentration under reduced pressure was carried out to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/ethanol=9/1) to obtain 1.15 g of the desired product (melting point: 165-167° C.).

Workup

  1. customthe reaction liquid
  2. waitwas left
  3. temperatureto cool
  4. additionwere added
  5. stirringby stirring
  6. extractionextraction with ethyl acetate
  7. concentrationThen, concentration under reduced pressure
  8. customto obtain a crude product
  9. customThe crude product was purified by silica gel column chromatography (eluent: ethyl acetate/ethanol=9/1)

Sources & evidence

ORD record
ord-abb353c06e144944a94fa48171d2405c
Source dataset
uspto-grants-2013_07
Patent number
US08481744B2

Reaction notes

Loading…