Toluene → N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]urea

HRID 1293005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1293005
[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[C@H:33]([OH:34])[C@H:32]([OH:35])[C@@H:31]([CH2:36][OH:37])[O:30]2)=[C:22]([NH:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:21]=1.C1(C)C=CC=CC=1.C(O)(C)C>ClCCl>[OH:34][C@@H:33]1[C@H:32]([OH:35])[C@@H:31]([CH2:36][OH:37])[O:30][C@H:29]1[N:26]1[CH:25]=[N:24][C:23]2[C:27]1=[N:28][C:20]([CH2:19][NH:18][C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:15]([CH3:17])[CH3:16])[CH:1]([CH3:2])[CH3:3])=[O:9])=[N:21][C:22]=2[NH:38][CH2:39][CH:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 3776IsopropanolHCID 21978296N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamideHCID 59875479(2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol

Produkt 1

HCID 9874284N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]ureaAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N-[2-(Diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (84 mg, 0.35mmol) (Preparation 27) was added to a stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol (150 mg, 0.35mmol) (Preparation 2) in dichloromethane (5 ml) at room temperature. The reaction was heated under reflux for 1 hour and then toluene (5 ml) and isopropanol (2 ml) were added. The dichloromethane was boiled off and the reaction was then heated under reflux for 1 hour. 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). This gave the title compound as a foam (60 mg).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe reaction was then heated
  4. temperatureunder reflux for 1 hour
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8f334656966a464ca8f141f00d28b5d3
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238676B2

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