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

反応式

HRID 2101306 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30280affddbc4ba8a2aafbacf7f5686f
出典データセット
uspto-grants-2009_08
特許番号
US07572808B2

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