Dimethyl malonate → HCID 136348491, compound

HRID 510377Notes

Reaction equation

HRID 510377 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][C:13]1[C:14]([NH2:18])=[N:15][NH:16][CH:17]=1.[C:19](OC)(=[O:25])[CH2:20][C:21](OC)=[O:22].C[O-].[Na+]>CO>[CH3:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][C:13]1[CH:17]=[N:16][N:15]2[C:21](=[O:22])[CH2:20][C:19](=[O:25])[NH:18][C:14]=12

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 178422938HCID 178422938, compound

Product 1

HCID 136348491HCID 136348491, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine (1.71 g, 6.7 mmol) in methanol (10 mL) was added dimethyl malonate (0.93 g, 7.0 mmol), followed by adding a 25% sodium methoxide solution (2.95 g, 13.40 mmol). The reaction vessel was sealed and irradiated (microwave) to 125° C. for 45 minutes. After the reaction mixture was cooled, precipitate was collected by filtration. The solid was washed with cooled methanol (5 mL×2). Product was dried under air. The product was then suspended with 1 N HCl (30 mL), stirred for 10 minutes. Product was obtained by filtration. It was dried under vacuum oven and was used in next step. (2.13 g, 98%). LC/MS: MS (ES+) m/e 324 (MH+)

Workup

  1. customThe reaction vessel was sealed
  2. customirradiated (microwave) to 125° C. for 45 minutes
  3. temperatureAfter the reaction mixture was cooled
  4. filtrationprecipitate was collected by filtration
  5. washThe solid was washed with cooled methanol (5 mL×2)
  6. customProduct was dried under air
  7. customProduct was obtained by filtration
  8. customIt was dried under vacuum oven

Sources & evidence

ORD record
ord-1baed850577249ed916876455db3bb6f
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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