Hydrochloric Acid → 3-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile
反応式
[C:1]([CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([OH:16])=O)=[CH:13][C:8]=2[N:7]=[CH:6]1)#[N:2].C1C=CC2N(O)N=NC=2C=1.Cl.CC[N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32].CCN=C=NCCCN(C)C.Cl.CN([CH:52]=[O:53])C>>[OH:53][CH:52]1[CH2:35][CH:34]2[N:30]([C:14]([C:12]3[CH:11]=[CH:10][C:9]4[N:5]([CH2:4][CH2:3][C:1]#[N:2])[CH:6]=[N:7][C:8]=4[CH:13]=3)=[O:16])[CH:31]([CH2:32][CH2:36]2)[CH2:33]1参加物
7
反応物 6
生成物 1
実験手順
To a solution of 1-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid (0.25 g, 1.16 mmol) in DMF (2.5 mL) was added with stirring HOBt (0.17 g, 1.27 mmol) followed by exo-nortropinol hydrochloride (0.21 g, 1.27 mmol), DIPEA (0.45 g, 3.48 mmol). EDCl.HCl was then added and it was stirred at room temperature for 12 h. The solvent was then evaporated and to the residue diluted with water (5 mL) and extracted with CH2Cl2. The organic phase was washed with brine solution, dried (Na2SO4) and the solvent evaporated. The residue was purified by preparative HPLC which afforded 0.26 g (67%) of 3-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile. MS-ESI m/z 325 (M+1).
後処理
- customThe solvent was then evaporated and to the residue
- additiondiluted with water (5 mL)
- extractionextracted with CH2Cl2
- washThe organic phase was washed with brine solution
- dry with materialdried (Na2SO4)
- customthe solvent evaporated
- customThe residue was purified by preparative HPLC which
出典と根拠
- ORDレコード
- ord-70da5a04389a435099296b11e06fea50
- 出典データセット
- uspto-grants-2011_11
- 特許番号
- US08053431B2
反応ノート
読み込み中…