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8-Hydroxyquinoline → 5-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide

HRID 643031
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HRID 643031 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]4=[O:23])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 685109935-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamideHCID 178516071HCID 178516071, 화합물

생성물 1

HCID 592601025-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide수율 32.4%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

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온도
130 °C

실험 절차

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide (200 mg, 0.451 mmol), 2-hydroxypyridine (85 mg, 0.90 mmol), 8-hydroxyquinoline (30 mg, 0.21 mmol) and K2CO3 (247 mg, 1.79 mmol) in DMSO (2 mL) was degassed with Argon before being charged with CuI (43 mg, 0.22 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the title compound (60 mg). MS 411.0 and 413.0 (M+H, Cl pattern).

후처리

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

출처 및 근거

ORD 기록
ord-12496b2b4bfd4ec796fd85f312e48960
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696352B2

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