Sodium Chloride → N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500066
[C:1]([BH3-])#[N:2].[Na+].[C:5]([C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2N(C)[N:21]=[C:20]([C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[C:19]=2[C:31]([F:34])([F:33])[F:32])=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14])(=O)[CH3:6].C([O-])(=O)C.[NH4+:39].[Cl-].[Na+]>CO>[NH2:39][CH:5]([C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2[N:2]([CH3:1])[N:21]=[C:20]([C:24]([F:30])([F:29])[C:25]([F:28])([F:26])[F:27])[C:19]=2[C:31]([F:32])([F:34])[F:33])=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14])[CH3:6]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 89650518N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Produkt 1

HCID 89650757N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamideAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (163 mg, 2.59 mmol, 3.0 eq.) was added to a solution of N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (400 mg, 0.863 mmol) and ammonium acetate (1.33 g, 17.3 mmol, 20 eq.) in methanol (15 ml). The mixture was stirred at room temperature for 4 h and then heated to 80° C. and kept at this temperature for 3 h. The mixture was cooled to room temperature and left overnight. Sat. aq. sodium chloride solution was added, the mixture was extracted with ethyl acetate and the extract was washed with sat. aq. sodium chloride solution and dried over MgSO4. After concentration under reduced pressure, the product was purified by column chromatography (hexane/ethyl acetate) to give N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (186 mg, 46%).

Aufarbeitung

  1. temperatureheated to 80° C.
  2. waitkept at this temperature for 3 h
  3. temperatureThe mixture was cooled to room temperature
  4. waitleft overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe extract was washed with sat. aq. sodium chloride solution
  7. dry with materialdried over MgSO4
  8. concentrationAfter concentration under reduced pressure
  9. customthe product was purified by column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-200b94699b944e538ba242e2d224e45b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09204645B2

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