Acetic Acid → 3-[6-Chloro-2-(ethylamino)-3-pyridinyl]-2-cyano-3-hydroxy-N-methyl-2-propenamide
反応式
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:9])[CH2:6][C:7]#[N:8].[H][H].NCC[C:15]1[N:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](F)=[O:18].[C:25](O)(=O)[CH3:26].C[N:30](C)C=O>>[Cl:24][C:22]1[N:23]=[C:15]([NH:30][CH2:25][CH3:26])[C:16]([C:17]([OH:18])=[C:6]([C:7]#[N:8])[C:5]([NH:4][CH3:3])=[O:9])=[CH:20][CH:21]=1参加物
反応物 6
生成物 1
実験手順
3.98 g (100 mmol) of sodium hydride at 60% in mineral oil are added, in small amounts, to a solution, cooled to 0-5° C., of 9.80 g (100 mmol) of N-methylcyanoacetamide in 100 ml of anhydrous dimethylformamide. Once no more hydrogen is being given off, the mixture is stirred for 10 minutes at ambient temperature, and is then cooled again to 0-5° C. A solution of 10.09 g (49.8 mmol) of 2-(aminoethyl)-6-chloronicotinic acid fluoride in 60 ml of dimethylformamide is then added and the medium is stirred at ambient temperature overnight. 2.85 ml (49.8 mmol) of acetic acid are added and the volatile compounds are evaporated off under reduced pressure. The residue is taken up in water and the product is extracted twice with a dichloromethane:methanol (95:5) mixture and then once with an ethyl acetate:THF (2:1) mixture. The combined organic phases are dried over MgSO4 and then the solvents are evaporated off under reduced pressure. 19.0 g of product are obtained, which product is used as it is in the next step.
後処理
- temperatureis then cooled again to 0-5° C
- stirringthe medium is stirred at ambient temperature overnight
- customthe volatile compounds are evaporated off under reduced pressure
- extractionthe product is extracted twice with a dichloromethane:methanol (95:5) mixture
- dry with materialThe combined organic phases are dried over MgSO4
- customthe solvents are evaporated off under reduced pressure
出典と根拠
- ORDレコード
- ord-ac039b1121cc41a3acb380b519be5160
- 出典データセット
- uspto-grants-2013_06
- 特許番号
- US08470847B2
反応ノート
読み込み中…