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8-Hydroxyquinoline → 5-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide

HRID 643038
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HRID 643038 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[CH:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[N:12]=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:15]=[CH:14][N:13]([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)[N:12]=2)=[O:8])=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 685066795-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamideHCID 178516071HCID 178516071, 화합물

생성물 1

HCID 592601105-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide수율 26.1%

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-3-yl)methyl)thiophene-2-carboxamide (60 mg, 0.14 mmol), 2-hydroxypyridine (30 mg, 0.32 mmol), 8-hydroxyquinoline (10 mg, 0.070 mmol) and K2CO3 (50 mg, 0.36 mmol) in DMSO (1 mL) was degassed with Argon before being charged with CuI (15 mg, 0.080 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the titled compound (15 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-8977820ed9ee4f868aca5b6b8d9919a3
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696352B2

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