N,N'-Dimethylethylenediamine → 5-Chloro-N-((1-(5-(2-oxopyridin-1(2H)-yl)pyridin-2-yl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 643010

反応式

HRID 643010 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[N:10]=[CH:9]2)=[N:6][CH:7]=1.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.CNCCNC.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O1CCOCC1.[Cu]I>[Cl:22][C:19]1[S:18][C:17]([C:15]([NH:14][CH2:13][C:11]2[N:10]=[CH:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([N:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]4=[O:23])=[CH:7][N:6]=3)[CH:12]=2)=[O:16])=[CH:21][CH:20]=1

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 68507465N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamideHCID 178516071HCID 178516071、化合物

生成物 1

HCID 249872595-Chloro-N-((1-(5-(2-oxopyridin-1(2H)-yl)pyridin-2-yl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide収率 6.6%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A mixture of N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide (42 mg, 0.11 mmol), 2-hydroxypyridine (40 mg, 0.42 mmol), N,N′-dimethylethylenediamine (0.035 mL, 0.32 mmol) and K2CO3 (52 mg, 0.38 mmol) in DMSO (1 mL) and dioxane (1 mL) was degassed with Argon before being charged with CuI (23 mg, 0.12 mmol). The mixture was heated at 110° C. overnight in a sealed tube. It was then purified by HPLC to give the title compound (3 mg). MS found for C19H14ClN5O2S: 412.2 and 414.2 (M+H, Cl pattern).

後処理

  1. customwas degassed with Argon
  2. customIt was then purified by HPLC

出典と根拠

ORDレコード
ord-3de329def22e45adb61ceacb273dc475
出典データセット
uspto-grants-2010_04
特許番号
US07696352B2

関連ノート

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