Cesium carbonate → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-6-{[2-(propylamino)ethyl]amino}-1,2-benzisothiazole-3-carboxamide
反応式
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P([C:41]2[CH:46]=[CH:45]C=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65](Br)=[CH:66][C:61]=3[S:60][N:59]=1)=[O:57])[CH2:48]2.C(=O)([O-])[O-].[Cs+].[Cs+].N1CCCC1=O.C[N:81]1[CH2:85][CH2:84][NH:83]C1=O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65]([NH:81][CH2:85][CH2:84][NH:83][CH2:45][CH2:46][CH3:41])=[CH:66][C:61]=3[S:60][N:59]=1)=[O:57])[CH2:48]2参加物
7
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 100 °C
実験手順
Palladium (II) acetate (0.09 mmol) was added to a solution of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.14 mmol) in toluene (8 mL) and the reaction mixture was maintained until the contents completely dissolved. The resultant yellow solution was transferred to a mixture of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1,2-benzisothiazole-3-carboxamide (0.33 mmol), cesium carbonate (0.39 mmol) and 1-methyl-2-imidazolidinone 2-pyrrolidinone (0.500 mmol) under an atmosphere of nitrogen gas and the reaction mixture was heated at 100° C. for 16 h. The reaction mixture was filtered through Celite and concentrated. The residue was purified by HPLC, thus providing the product in 70% yield.
後処理
- temperaturethe reaction mixture was maintained until the contents
- dissolutioncompletely dissolved
- filtrationThe reaction mixture was filtered through Celite
- concentrationconcentrated
- customThe residue was purified by HPLC
- customthus providing the product in 70% yield
出典と根拠
- ORDレコード
- ord-1030cd2aa73f4544a5c7107d88eb0b2f
- 出典データセット
- uspto-grants-2013_07
- 特許番号
- US08486937B2
反応ノート
読み込み中…