Acetyl chloride → HCID 86633185, compound

HRID 1183910Notes

Reaction equation

HRID 1183910 reaction equation
C(Cl)(=O)C.[Br:5][C:6]1[CH:10]=[N:9][N:8]([CH3:11])[C:7]=1[C:12]1[CH:13]=[C:14]([NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]([CH3:25])([N+:22]([O-])=O)[CH3:21]>CO.[Zn]>[NH2:22][C:20]([CH3:25])([CH3:21])[CH2:19][O:18][C:17]1[CH:16]=[CH:15][C:14]([NH:26][C:27](=[O:32])[C:28]([F:31])([F:29])[F:30])=[CH:13][C:12]=1[C:7]1[N:8]([CH3:11])[N:9]=[CH:10][C:6]=1[Br:5]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 86633184HCID 86633184, compound

Product 1

HCID 86633185HCID 86633185, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

Acetylchloride (1.36 mL, 19.1 mmol) was added slowly to a well-stirred solution of N-(3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)phenyl)-2,2,2-trifluoroacetamide (889 mg, 1.91 mmol) in methanol (10 mL). Zinc dust (1.25 g, 19.1 mmol) was added in small portions, and the mixture was stirred at 55° C. After 2 h, the solvent was removed under reduced pressure, and residue was suspended in 1M HCl (10 mL) and covered with ethyl acetate. The mixture was cooled on an ice bath, and ammonium hydroxide was added until all precipitate dissolved. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried with sodium sulfate, filtered and evaporated to dryness to yield N-(4-(2-amino-2-methylpropoxy)-3-(4-bromo-2-methyl-2H-pyrazol-3-yl)phenyl)-2,2,2-trifluoroacetamide as a white powder (693 mg, 1.59 mmol, 83%). LCMS m/z (%)=437.3 (M+H 81Br 9.0%), 435.2 (M+H 79Br 14.0%).

Workup

  1. customthe solvent was removed under reduced pressure, and residue
  2. temperatureThe mixture was cooled on an ice bath
  3. additionammonium hydroxide was added until all precipitate
  4. dissolutiondissolved
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined ethyl acetate extracts were washed with brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-5252df5ea25f40d697a745212e348a4b
Source dataset
uspto-grants-2014_03
Patent number
US08664258B2

Reaction notes

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