Water → HCID 178464833, compound

HRID 1641442Notes

Reaction equation

HRID 1641442 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>[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

6

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 1

HCID 6228DimethylformamideSolvent

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, 460 mg of 2,3-dichloropyridine was added and then 350 mg of sodium hydride was added, followed by stirring for about 7 hours at about 70° C. in nitrogen atmosphere, and the reaction liquid was stood to cool. Water was added to the reaction liquid and stirred, followed by extraction with ethyl acetate, and the obtained crude product was purified by silica gel column chromatography (eluent: ethyl acetate/methanol=9/1) to obtain 1.15 g of the desired product.

Workup

  1. customthe reaction liquid
  2. temperatureto cool
  3. stirringstirred
  4. extractionfollowed by extraction with ethyl acetate
  5. customthe obtained crude product
  6. customwas purified by silica gel column chromatography (eluent: ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-9e63538964e742c1ac1c0f62f9a23fa5
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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