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Diisopropylethylamine → 3-(4-chlorophenyl)-1-[3-((4-chlorophenyl)sulfonyl)butanoyl]-4,5-dihydro-4-phenyl-1H-pyrazole

HRID 1016605
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HRID 1016605 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:49]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:48][NH:47][N:46]=2)=[CH:41][CH:40]=1>>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[CH:49]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:48][N:47]([C:13](=[O:15])[CH2:12][CH:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:9])=[O:10])[CH3:16])[N:46]=2)=[CH:43][CH:44]=1
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참가 물질

5

반응물 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27390873-(4-Chlorobenzenesulfonyl)butyric acidHCID 113688843-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole

생성물 1

HCID 112142203-(4-chlorophenyl)-1-[3-((4-chlorophenyl)sulfonyl)butanoyl]-4,5-dihydro-4-phenyl-1H-pyrazole수율 105.1%

실험 절차

To a stirred mixture of 3-((4-chlorophenyl)sulfonyl)butyric acid (1.85 gram, 7.00 mmol), diisopropylethylamine (3 ml) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.50 gram, 15.7 mmol) was added 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole (3.00 gram, 11.7 mmol) and the resulting mixture was stirred for 16 hours at room temperature. After concentration in vacuo the resulting residue was purified by flash chromatography (petroleum ether/diethyl ether=1/2 (v/v), followed by diethyl ether) to give 3-(4-chlorophenyl)-1-[3-((4-chlorophenyl)sulfonyl)butanoyl]-4,5-dihydro-4-phenyl-1H-pyrazole (3.69 gram, 63% yield) as a diastereomeric mixture. Melting point: amorphous.

후처리

  1. concentrationAfter concentration in vacuo the resulting residue
  2. customwas purified by flash chromatography (petroleum ether/diethyl ether=1/2 (v/v), followed by diethyl ether)

출처 및 근거

ORD 기록
ord-350e7035b7824fe79ec65675a03c6aa1
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06476060B2

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