1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58681715, Verbindung

HRID 10456

Reaktionsgleichung

Reaktionsgleichung von HRID 10456
[C:1]1([CH:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([OH:21])=O)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@H:22]2[C@H:26]([OH:27])[C@H:25]([OH:28])[C@@H:24]([C:29]([NH:31][CH2:32][CH3:33])=[O:30])[O:23]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:40][C:41]([F:52])([F:51])[C:42]([NH:44][CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)=[O:43].Cl.CN(C)CCCN=C=NCC>ClCCl>[C:1]1([CH:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([N:48]3[CH2:49][CH2:50][CH:45]([NH:44][C:42](=[O:43])[C:41]([F:51])([F:40])[F:52])[CH2:46][CH2:47]3)=[O:21])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:22]2[O:23][C@H:24]([C:29]([NH:31][CH2:32][CH3:33])=[O:30])[C@@H:25]([OH:28])[C@H:26]2[OH:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107742532,2,2-trifluoro-N-(piperidin-4-yl)acetamideHCID 183458936-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylic acid

Produkt 1

HCID 58681715HCID 58681715, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylic acid (Preparation 39) (0.2 g, 0.38 mmol), 2,2,2-trifluoro-N-(4-piperidinyl)acetamide (83 mg, 0.42 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (81 mg, 0.42 mmol) in dichloromethane (5 ml) was stirred at room temperature for 48 hours and then heated under reflux for a further 96 hours. The solution was allowed to cool to room temperature and then solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (95:5:1, by volume) changing to dichloromethane:methanol:concentrated aqueous ammonia (80:20:1, by volume). After evaporation of appropriate fractions the target compound was obtained as a white solid, (43 mg, 18%).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for a further 96 hours
  3. customsolvent removed by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  5. customAfter evaporation of appropriate fractions the target compound
  6. customwas obtained as a white solid, (43 mg, 18%)

Quellen und Nachweise

ORD-Eintrag
ord-061f27f5257242b2996f0872243ec48d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094769B2

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