HCID 21071120, compound → HCID 21071118, compound

HRID 270802Notes

Reaction equation

HRID 270802 reaction equation
[N:1]([CH2:4][C:5]1[N:9]([CH2:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[N:8]=[C:7]([C:26]([F:29])([F:28])[F:27])[C:6]=1[Cl:30])=[N+]=[N-]>CO>[NH2:1][CH2:4][C:5]1[N:9]([CH2:10][C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)=[O:12])[N:8]=[C:7]([C:26]([F:28])([F:27])[F:29])[C:6]=1[Cl:30]

Participants

3

Reactant 1

HCID 21071120HCID 21071120, compound

Product 1

HCID 21071118HCID 21071118, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.85 g (6.2 mmol) of 2-(5-Azidomethyl-4-chloro-3-trifluoromethyl-pyrazol-1-yl)-1-[4-(4-chlorophenyl)-piperazin-1-yl]-ethanone was dissolved in 80 mL methanol, and 3.61 g (16.0 mmol) of SnCl2 hydrate was added. After two hours, the reaction was concentrated in vacuo to remove the methanol. The residue was partitioned between 0.5M NaOH and ethyl acetate, and the phases were separated. The aqueous phase was back-extracted once with ethyl acetate. The combined ethyl acetate phases were extracted twice with 1M HCl. The acidic aqueous phase was basified with 1M NaOH, and was extracted once with ethyl acetate. The final ethyl acetate phase was washed once with brine, dried over Na2SO4, filtered, and concentrated to an oil. The oil was dissolved in methanol, acidified with 2M HCl in ether, and the product was isolated by filtration after precipitation: 1H NMR (DMSO-d6, 400 MHz) 8.58 (s, 3H), 7.27 (d, 2H), 7.03 (d, 2H), 5.71 (s, 2H), 4.10 (d, 2H), 3.64 (m, 4H), 3.32 (m, 2H), 3.19 (m, 2H) ppm; MS (ES) M+H expected=436.1, found=436.0.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customto remove the methanol
  3. customThe residue was partitioned between 0.5M NaOH and ethyl acetate
  4. customthe phases were separated
  5. extractionThe aqueous phase was back-extracted once with ethyl acetate
  6. extractionThe combined ethyl acetate phases were extracted twice with 1M HCl
  7. extractionwas extracted once with ethyl acetate
  8. washThe final ethyl acetate phase was washed once with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated to an oil
  12. dissolutionThe oil was dissolved in methanol
  13. customthe product was isolated by filtration
  14. customafter precipitation

Sources & evidence

ORD record
ord-1a829ca87a34447c97292e9298778412
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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