反応式
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]3[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]3[CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([N:12]3[CH2:17][CH2:16][N:15]4[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]4[CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a stirred solution of N-((3-chloropyrazin-2-yl)methyl)-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxamide (1.25 g, 3.46 mmol) in Acetonitrile (10 ml) was added pyridine (2.73 g, 34.6 mmol) and finally phosphoryl trichloride (2.65 g, 17.28 mmol). The resulting reaction mixture was then stirred at room temperature for 15 hours overnight. The reaction was quenched by slowly addition of NaHCO3 and extracted with ethyl acetate (3×). The organic layer was dried by MgSO4, filtered and concentrated. The residue was purified by MPLC (24 g silica gel, 20 to 60% ethyl acetate in hexaes, 18 CV) to afford white solid product 7-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (550 mg, 1.600 mmol, 46.3% yield). LC-MS: C12H9ClF3N7,343. found 344.11 [M+H]+, RT=1.22 min.
後処理
- customThe resulting reaction mixture
- customThe reaction was quenched by slowly addition of NaHCO3
- extractionextracted with ethyl acetate (3×)
- dry with materialThe organic layer was dried by MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by MPLC (24 g silica gel, 20 to 60% ethyl acetate in hexaes, 18 CV)
出典と根拠
- ORDレコード
- ord-d5580530d4b4407ea6c6d50ee0ad01d4
- 出典データセット
- uspto-grants-2016_09
- 特許番号
- US09446130B2
関連ノート
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