Dimethylformamide → 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one
反応式
[C:1](NCC(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:13](N1C=CN=C1)([N:15]1C=CN=C1)=O.[Cl:25][C:26]1[C:31]2[C:32](=[O:45])[N:33]([CH3:44])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3[C:40](=[N:42][OH:43])[NH2:41])[C:30]=2[CH:29]=[CH:28][CH:27]=1.[CH3:46]N(C)C=O>>[C:1]([C:46]1[O:43][N:42]([CH2:13][NH2:15])[CH:40]([C:39]2[N:38]=[CH:37][N:36]3[C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:25])[C:31]=4[C:32](=[O:45])[N:33]([CH3:44])[CH2:34][C:35]=23)[N:41]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]参加物
反応物 4
生成物 1
実験手順
2.45 g (14 mmol) of BOC-glycine were dissolved in 20 ml of N,N-dimethylformamide, whereupon the mixture was treated portionwise with 2.43 g (15 mmol) of 1,1'-carbonyldiimidazole and stirred at 50° for 20 min. After adding 3.8 g (12.4 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime the mixture was stirred at 90° overnight. The reaction mixture was concentrated; the residue was dissolved in methylene chloride and washed three times with water. After drying the solution, evaporation of the solvent and crystallization of the residue from ethyl acetate and hexane there were obtained 5.33 g (96%) of 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 144°-146°.
後処理
- stirringwas stirred at 90° overnight
- concentrationThe reaction mixture was concentrated
- dissolutionthe residue was dissolved in methylene chloride
- washwashed three times with water
- customAfter drying
- customthe solution, evaporation of the solvent and crystallization of the residue from ethyl acetate
出典と根拠
- ORDレコード
- ord-f96b7f12d8824bdbb604f11449c8e8ca
- 出典データセット
- uspto-grants-1997_09
- 特許番号
- US05665718
反応ノート
読み込み中…