Ammonium formate → 6-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-(4-piperidinyl)-9H-purine-2-carboxamide

HRID 353636

Reaktionsgleichung

Reaktionsgleichung von HRID 353636
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:25]=[C:24]3[C:20]([N:21]=[CH:22][N:23]3[C@H:26]3[C@H:30]([OH:31])[C@H:29]([OH:32])[C@@H:28]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[O:27]3)=[C:19]([NH:38][CH2:39][CH:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:18]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[C:41]1([CH:40]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:39][NH:38][C:19]2[N:18]=[C:17]([C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:16])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@H:26]2[C@H:30]([OH:31])[C@H:29]([OH:32])[C@@H:28]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[O:27]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 60091679N-(1-Benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide

Produkt 1

HCID 600916826-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-(4-piperidinyl)-9H-purine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(1-benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 33) (1.03 g, 1.47 mmol), palladium (II) hydroxide (0.9 g) and ammonium formate (0.46 g, 7.3 mmol) in ethanol (10 ml) was heated under reflux for 3 hours. The catalyst was removed by filtration through Arbocel (trade mark), solvent removed by evaporation under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of dichioromethane:methanol:concentrated aqueous ammonia (90:10:1, by volume) changing to dichloromethane:methanol:concentrated aqueous ammonia (80:20:2, by volume). After evaporation of appropriate fractions the target compound was obtained as a white solid, (0.6 g, 67%).

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. customThe catalyst was removed by filtration through Arbocel (trade mark), solvent
  3. customremoved by evaporation under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a gradient system of dichioromethane
  5. customAfter evaporation of appropriate fractions the target compound
  6. customwas obtained as a white solid, (0.6 g, 67%)

Quellen und Nachweise

ORD-Eintrag
ord-6a2addd94b90499aa90803362d9b0078
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753322B2

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