Toluene → (2S,3S,4R,5R)-5-{2-{[({[2-(Diisopropylamino)ethyl]amino}carbonyl)amino]methyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 897074노트

반응식

HRID 897074 반응식
[CH:1]([N:4]([CH:15]([CH3:17])[CH3:16])[CH2:5][CH2:6][NH:7][C:8](N1C=CN=C1)=[O:9])([CH3:3])[CH3:2].[NH2:18][CH2:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[C@@H:29]2[O:33][C@H:32]([C:34]([NH:36][CH2:37][CH3:38])=[O:35])[C@@H:31]([OH:39])[C@H:30]2[OH:40])=[C:22]([NH:41][CH2:42][CH:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:21]=1.C(O)(C)C.C1(C)C=CC=CC=1>ClCCl.C(OCC)C>[CH:15]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][NH:7][C:8]([NH:18][CH2:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[C@@H:29]2[O:33][C@H:32]([C:34]([NH:36][CH2:37][CH3:38])=[O:35])[C@@H:31]([OH:39])[C@H:30]2[OH:40])=[C:22]([NH:41][CH2:42][CH:43]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[N:21]=1)=[O:9])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 3776IsopropanolHCID 21978296N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamideHCID 59909598(2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

생성물 1

HCID 10122714(2S,3S,4R,5R)-5-{2-{[({[2-(Diisopropylamino)ethyl]amino}carbonyl)amino]methyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide수율 44.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매3회

실험 절차

N-[2-(Diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (84 mg, 0.35 mmol) (Preparation 27) was added to a stirred suspension of (2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (100 mg, 0.23 mmol) (Preparation 11) in dichloromethane (5 ml) at room temperature. The reaction was then heated to reflux and a drop of isopropanol was added to help dissolve the reagents. The reaction mixture was heated under reflux for 20 minutes and then toluene (5 ml) was added. The dichloromethane was boiled off and the reaction was then heated under reflux for 30 minutes. The reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume increasing to 80:20:2 by volume). The solvent was removed under reduced pressure to give a yellow oil. The oil was dissolved in dichloromethane (2 ml) and diethylether was added to induce crystallisation. Filtration gave the title compound as a white solid (70 mg).

후처리

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. dissolutionto help dissolve the reagents
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 20 minutes
  6. temperaturethe reaction was then heated
  7. temperatureunder reflux for 30 minutes
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  10. customThe solvent was removed under reduced pressure
  11. customto give a yellow oil
  12. customcrystallisation
  13. filtrationFiltration

출처 및 근거

ORD 기록
ord-f3315116d94a4bf28c6073cb093d0ddf
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921753B2

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