Hydrochloric Acid → (S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one

HRID 1527973노트

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HRID 1527973 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][C:13]=2[O:18]C)=[O:11])=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[C:13](=[O:18])[NH:14][N:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 86684800(S)-3-(4-Bromophenyl)-1-(3-methoxypyridazin-4-yl)-3-o-tolylpropan-1-one

생성물 1

HCID 86684801(S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one수율 108.4%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

To a solution of (S)-3-(4-bromophenyl)-1-(3-methoxypyridazin-4-yl)-3-o-tolylpropan-1-one (example 4, step 1; 312 mg, 759 μmol) in 1,4-dioxane (9 ml) was added 37% aq. hydrochloric acid solution (1.27 ml, 15.2 mmol) and the resulting solution was first stirred at 60° C. for 3 h and then for 2½ h at 80° C. After cooling the reaction mixture was poured onto ice water and ethyl acetate, neutralized with sat. aq. sodium hydrogen carbonate solution and the pH was adjusted to 6.85 with 1 M aq. potassium phosphate buffer solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound (327 mg, quantitative), which was directly used in the next step. Light red foam, MS: 397.1 [M+H]+.

후처리

  1. waitfor 2½ h at 80° C
  2. temperatureAfter cooling the reaction mixture
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-e88cb08bba59434da709ff9c82be9d36
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090565B2

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