Tetronic acid → 4-[[(6-Chloro-5-fluoropyridin-3-yl)methyl](methyl)amino]furan-2(5h)-one

HRID 425751ノート

反応式

HRID 425751 の反応式
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=O.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][NH:16][CH3:17])=[CH:11][C:10]=1[F:18]>C(O)(=O)C>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:17])[C:2]2[CH2:4][O:5][C:6](=[O:7])[CH:1]=2)=[CH:11][C:10]=1[F:18]

参加物

4

反応物 2

HCID 521261Tetronic acidHCID 86634700((6-Chloro-5-fluoropyridin-3-yl)methyl)(methyl)amine

生成物 1

HCID 251910444-[[(6-Chloro-5-fluoropyridin-3-yl)methyl](methyl)amino]furan-2(5h)-one収率 52%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

24.80 g (248 mmol) of tetronic acid are added slowly to 41.40 g (225.3 mmol) of N-[(6-chloro-5-fluoropyridin-3-yl)methyl]methanamine (III-1) in 64 ml of acetic acid, and the mixture is stirred at room temperature for about 16 hours. The reaction mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution and dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by recrystallization from ethyl acetate gives 30.0 g (52% of theory) of 4-[[(6-chloro-5-fluoropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one.

後処理

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. washthe mixture is washed successively twice with 1 N aqueous hydrochloric acid, twice with 1 N aqueous sodium hydroxide solution and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customConcentration of the organic phase under reduced pressure and purification of the residue
  5. customby recrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-441e1f78251b4448b30cb41ca5474081
出典データセット
uspto-grants-2012_01
特許番号
US08106212B2

反応ノート

読み込み中…