反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[NH2:20])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[O:28]=[C:29](Cl)OC(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([N:12]2[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[NH:20][C:29]2=[O:28])[CH2:10][CH2:11]1)=[O:5])[CH3:2]参加物
実験手順
To a solution of 4-(2-amino-4-fluoro-phenylamino)-piperidine-1-carboxylic acid ethyl ester (0.100 g, 0.36 mmol) and triethylamine (0.110 mg, 1.08 mmol) in methylene chloride (2 mL) at 0° C. was added a solution of diphosgene (0.71 mg, 0.36 mmol) in methylene chloride (4 mL) at room temperature. The reaction mixture was stirred for 18 h then quenched with a saturated aqueous solution of sodium bicarbonate. The organic phase was separated and washed with brine. The organic phase was purified by passing it through a plug of silica gel, using ethyl acetate as the eluent. The filtrate was evaporated, in vacuo, to a residue. The residue was triturated with hexanes/dichlormethane (95:5) and the solid collected by filtration. Vaccum drying yielded 4-(5-fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic acid ethyl ester (77.8 mg, 71%) as a light tan solid.
後処理
- customthen quenched with a saturated aqueous solution of sodium bicarbonate
- customThe organic phase was separated
- washwashed with brine
- customThe organic phase was purified
- customThe filtrate was evaporated, in vacuo, to a residue
- customThe residue was triturated with hexanes/dichlormethane (95:5)
- filtrationthe solid collected by filtration
- customVaccum drying
出典と根拠
- ORDレコード
- ord-24daf4245463488390dc24555c4d9202
- 出典データセット
- uspto-grants-2007_07
- 特許番号
- US07244744B2
関連ノート
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