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

반응식

HRID 2101306 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-30280affddbc4ba8a2aafbacf7f5686f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572808B2

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