Dimethyl acetylsuccinate → HCID 178499495, compound

HRID 472845Notes

Reaction equation

HRID 472845 reaction equation
[Cl:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[NH2:7].[C:9]([CH:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:13](OC)=[O:14])(=O)[CH3:10]>C1(C)C(C)=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[C:3]([CH3:8])=[N:4][N:5]2[C:13]([OH:14])=[C:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9]([CH3:10])=[N:7][C:6]=12

Participants

5

Reactant 2

HCID 112039Dimethyl acetylsuccinateHCID 13807164-chloro-5-methyl-1H-pyrazol-3-amine

Product 1

HCID 178499495HCID 178499495, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 7237O-XyleneSolvent

Procedure

To a solution of 4-chloro-3-methyl-1H-pyrazol-5-amine (0.263 g, 2 mmol) and dimethyl 2-acetylsuccinate (1.3 g, 6 mmol) in xylene (50 mL) was added p-toluenesulfonic acid monohydrate (4 mg, 0.02 mmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 2 hrs. The solid was filtered and washed by hexanes to afford (0.31 g, 58%) of the title compound. 1H-NMR (500 MHz, DMSO-d6) δ ppm 2.28 (s, 3H), 2.33 (s, 3H), 3.54 (s, 2H), 3.61 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 2 hrs
  3. filtrationThe solid was filtered
  4. washwashed by hexanes

Sources & evidence

ORD record
ord-09fdb539d9e642ce92da912e681e5e60
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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