Hydroxyamine hydrochloride → 7-(4-chlorophenyl)-8-(4-(1-(hydroxyimino)ethyl)phenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101306

Reaktionsgleichung

Reaktionsgleichung von HRID 2101306
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[N:12]([C:23](=[O:37])[N:24]([CH2:26][C:27]4[CH:28]=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=4)[N:25]=3)[CH:13]=[CH:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[NH2:39][OH:40]>C1COCC1.O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]2[CH:14]=[CH:13][N:12]3[C:23](=[O:37])[N:24]([CH2:26][C:27]4[CH:28]=[N:29][C:30]([C:33]([F:35])([F:34])[F:36])=[CH:31][CH:32]=4)[N:25]=[C:11]3[C:10]=2[C:7]2[CH:8]=[CH:9][C:4]([C:1](=[N:39][OH:40])[CH3:2])=[CH:5][CH:6]=2)=[CH:21][CH:20]=1

Komponenten

5

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 160051638-(4-acetylphenyl)-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Produkt 1

HCID 732186687-(4-chlorophenyl)-8-(4-(1-(hydroxyimino)ethyl)phenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 8-(4-acetylphenyl)-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (43.3 mg, 0.083 mmol) in THF (2 mL) and water (2 mL) at room temperature was added hydroxylamine hydrochloride (11.5 mg, 0.17 mmol). After 108 h, the reaction mixture was diluted with water and extracted twice with EtOAc. The organic extracts are combined, dried (MgSO4), filtered and evaporated. Purification by preparative reverse phase HPLC (methanol-water-trifluoroacetic acid), pooling the fractions, evaporating, redissolving the residuum in dichloromethane, washing with saturated aq. NaHCO3 solution, drying (MgSO4), filtering and evaporating provided the title compound as a yellow solid, 38 mg, 85%. HPLC/MS: retention time=3.38 min, [M+H]+=538. 1H NMR (CDCl3): δ 8.79 (d, J=1.8 Hz, 1H), 8.62 (br s, 1H), 7.92 (dd, J=1.8, 8.0 Hz, 1H), 7.84 (d, J=7.0 Hz, 2H), 7.66 (d, J=7.9 Hz, 1H), 7.57 (dd, J=2.2, 6.6 Hz, 2H), 7.23 (m, 5H), 7.06 (d, J=6.6 Hz, 2H), 6.65 (d, J=7.1 Hz, 1H), 5.27 (s, 2H), 2.25 (s, 3H).

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by preparative reverse phase HPLC (methanol-water-trifluoroacetic acid)
  6. customevaporating
  7. dissolutionredissolving the residuum in dichloromethane
  8. washwashing with saturated aq. NaHCO3 solution
  9. dry with materialdrying (MgSO4)
  10. filtrationfiltering
  11. customevaporating

Quellen und Nachweise

ORD-Eintrag
ord-30280affddbc4ba8a2aafbacf7f5686f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572808B2

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