Acetyl chloride → N-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-(2-ethylamino-2-methyl-propoxy)-phenyl]-3-trifluoromethyl-benzamide

HRID 1685683Notes

Reaction equation

HRID 1685683 reaction equation
[C:1](Cl)(=O)[CH3:2].[N+:5]([C:8]([CH3:38])([CH3:37])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)=[CH:13][C:12]=1[C:30]1[N:31]([CH3:36])[N:32]=[CH:33][C:34]=1[Cl:35])([O-])=O>CO.[Zn]>[Cl:35][C:34]1[CH:33]=[N:32][N:31]([CH3:36])[C:30]=1[C:12]1[CH:13]=[C:14]([NH:17][C:18](=[O:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH:15]=[CH:16][C:11]=1[O:10][CH2:9][C:8]([NH:5][CH2:1][CH3:2])([CH3:38])[CH3:37]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 67265611HCID 67265611, compound

Product 1

HCID 24888500N-[3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-(2-ethylamino-2-methyl-propoxy)-phenyl]-3-trifluoromethyl-benzamide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

Acetyl chloride (388 μl, 5.44 mmol) was added dropwise to a solution of N-(4-(2-nitro-2-methylpropoxy)-3-(4-chloro-2-methyl-2H-pyrazol-3-yl)phenyl)-3-(trifluoromethyl)benzamide (270 mg, 0.544 mmol) in methanol (5.0 mL). Zinc dust (356 mg, 5.44 mmol) was added, and the mixture was stirred at 23° C. After 1 hour, the mixture was filtered and the filtrate was evaporated to dryness. The residue was taken up in ammonium hydroxide (35%), diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered, and evaporated to dryness to afford the title compound as a colorless foam which was used without further purification. LCMS m/z (%) 469.4 (M+H, 37Cl 46.9), 467.2 (M+H, 35Cl 86.1), 452.2 (51.6%), 450.1 (100.0%).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-582eda47e6514a52845f56cfb896d355
Source dataset
uspto-grants-2012_04
Patent number
US08148418B2

Reaction notes

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