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Diisopropylethylamine → [1-[(4-Fluorophenyl)methyl]benzimidazol-2-yl]-[1-[2-[3-phenyl-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]methanone

HRID 2269850
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HRID 2269850 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].[F:32][C:33]1[CH:56]=[CH:55][C:36]([CH2:37][N:38]2[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[N:40]=[C:39]2[C:47]([CH:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[O:48])=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C.CO>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:52]2[CH2:53][CH2:54][CH:49]([C:47]([C:39]3[N:38]([CH2:37][C:36]4[CH:35]=[CH:34][C:33]([F:32])=[CH:56][CH:55]=4)[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=4[N:40]=3)=[O:48])[CH2:50][CH2:51]2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 155428881-(3,4,5-Trimethoxy-benzoyl)-3-phenyl-3-(2-methanesulfonyl-ethyl)-pyrrolidineHCID 21584119Ethylacetate methanol

생성물 1

HCID 10212223[1-[(4-Fluorophenyl)methyl]benzimidazol-2-yl]-[1-[2-[3-phenyl-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]methanone

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-phenyl-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.60 g, 1.30 mmol) and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.66 g, 1.95 mmol), and diisopropylethylamine (0.453 mL, 2.60 mmol) in chlorobenzene (8 mL). Heat to reflux. After 18 hours, partition the residue between ethyl acetate and water. Extract the organic layer 3 times with water and 1 time with saturated sodium chloride solution. Dry the organic layer over Na2So4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonium hydroxide to give the title compound: Rf=0.15 (silica gel, 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonium hydroxide).

후처리

  1. temperatureHeat to reflux
  2. custompartition the residue between ethyl acetate and water
  3. extractionExtract the organic layer 3 times with water and 1 time with saturated sodium chloride solution
  4. customDry the organic layer over Na2So4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

출처 및 근거

ORD 기록
ord-b05ea48af79e41b6b142dc9ee3a03b33
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06329392B1

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