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

반응식

HRID 643010 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3de329def22e45adb61ceacb273dc475
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696352B2

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