Hydrochloric Acid → [4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 1804065ノート

反応式

HRID 1804065 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1.[OH-].[Na+].Cl.[CH3:22][C:23]1[C:24]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:25][CH:26]=[C:27]([CH3:29])[CH:28]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([N:33]2[CH2:34][CH2:35][N:30]([C:24]3[C:23]([CH3:22])=[CH:28][C:27]([CH3:29])=[CH:26][N:25]=3)[CH2:31][CH2:32]2)=[O:8])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazineHCID 58484624Methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate

生成物 1

HCID 58484716[4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone収率 81.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

To methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate (2 g) described in Preparation Example 116 were added 1N aqueous sodium hydroxide solution (9 mL) and methanol (18 mL), and the mixture was stirred at 60-70° C. 1N hydrochloric acid (9 mL) was added, a solution of 1-(3,5-dimethylpyridin-2-yl)piperazine (1.14 g) described in Preparation Example 47 in methanol (2 mL) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.65 g) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporation of the solvent, the residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (2.4 g).

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by column chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-0942c41825b241d28e1d6abbd6c64dda
出典データセット
uspto-grants-2013_01
特許番号
US08354401B2

反応ノート

読み込み中…