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Potassium Carbonate → 8-Chloro-7-(4-chlorophenyl)-2-(pyrazin-2-ylmethyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

HRID 2224273
ノート
印刷プレビュー

反応式

HRID 2224273 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:26][C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)[N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 170169Pyrazine, 2-(chloromethyl)-HCID 597166868-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

生成物 1

HCID 597167678-Chloro-7-(4-chlorophenyl)-2-(pyrazin-2-ylmethyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one収率 74%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of 8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (0.62 g, 2.21 mmol), prepared as described in Example 354, in DMF (10 mL) at RT was added K2CO3 (0.61 g, 4.4 mmol) and 2-(chloromethyl)pyrazine (0.83 g). The reaction mixture was heated at 50° C. for 2 h. After this time, the mixture was diluted with EtOAc (150 mL). The resultant solution was washed with water and saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with hexanes:EtOAc 1:2 to afford 0.61 g of the title compound, 8-chloro-7-(4-chlorophenyl)-2-(pyrazin-2-ylmethyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one as a yellow solid. HPLC RT: 2.86 min; MS, M+H=373; 1H NMR (CDCl3): δ 8.64 (d, 1H), 8.54 (m, 2H), 8.11 (s, 1H), 7.54-7.49 (m, 4H), 5.48 (s, 2H).

後処理

  1. washThe resultant solution was washed with water and saturated aqueous NaCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with hexanes:EtOAc 1:2

出典と根拠

ORDレコード
ord-f6bbeb0c13c0403c86e627b21c6ed396
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07378418B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート