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 897074ノート

反応式

HRID 897074 の反応式
[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]

参加物

7

反応物 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

生成物 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-furancarboxamide収率 44.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f3315116d94a4bf28c6073cb093d0ddf
出典データセット
uspto-grants-2005_07
特許番号
US06921753B2

反応ノート

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