Acetonitrile → [1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]methanone

HRID 2269843노트

반응식

HRID 2269843 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].C(N(C(C)C)CC)(C)C.[F:43][C:44]1[CH:67]=[CH:66][C:47]([CH2:48][N:49]2[C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=3[N:51]=[C:50]2[C:58]([CH:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)=[O:59])=[CH:46][CH:45]=1.C(#N)C>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:63]2[CH2:64][CH2:65][CH:60]([C:58]([C:50]3[N:49]([CH2:48][C:47]4[CH:46]=[CH:45][C:44]([F:43])=[CH:67][CH:66]=4)[C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=4[N:51]=3)=[O:59])[CH2:61][CH2:62]2)([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:9]1)=[O:7]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 155428861-(3,4,5-Trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine

생성물 1

HCID 10190770[1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]methanone

시약·촉매·용매 1

HCID 21584119Ethylacetate methanol용매

실험 절차

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.48 g, 1.41 mmol), diisopropylethylamine (0.24 g, 1.9 mmol), 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.50 g, 0.94 mmol), and acetonitrile (15 mL). Heat to reflux. After 18 hours, cool and partition the reaction mixture between ethyl acetate and water. Extract the organic layer with a saturated sodium bicarbonate solution and a 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 12% methanol/ethyl acetate containing 0.1% concentrated aqueous ammonia solution to give the title compound: Rf=0.35 (silica gel, 12% methanol/ethyl acetate containing 0.1% concentrated aqueous ammonia solution).

후처리

  1. temperatureHeat to reflux
  2. temperaturecool
  3. custompartition the reaction mixture between ethyl acetate and water
  4. extractionExtract the organic layer with a saturated sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue

출처 및 근거

ORD 기록
ord-5c042e07c3444cb3b154be94d6f37a93
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329392B1

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