Sodium ethoxide → 8-Chloro-3-pentyl-1-{4-[5-(1,3-thiazol-2-yl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097697
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15]/[C:16](=[N:19]/[H])/[NH:17][OH:18])[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1.CC[O-].[Na+].[S:31]1[CH:35]=[CH:34][N:33]=[C:32]1[C:36](OCC)=O>CCO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[N:19]=[C:36]([C:32]4[S:31][CH:35]=[CH:34][N:33]=4)[O:18][N:17]=3)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 13032471Ethyl 1,3-thiazole-2-carboxylateHCID 178506473HCID 178506473, Verbindung

Produkt 1

HCID 593954418-Chloro-3-pentyl-1-{4-[5-(1,3-thiazol-2-yl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A solution of (1Z)-5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (50 mg, 0.13 mmol) in EtOH (1.5 ml) was treated with a 21% solution of NaOEt in EtOH (50 μl, 0.13 mmol) and ethyl 1,3-thiazole-2-carboxylate (18 mg, 0.11 mmol). The mixture was heated in the microwave at 170° C. for 10 min. After cooling, the reaction was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated then concentrated and purified by the MDAP. The title compound was obtained as a white solid (13 mg, 21%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between 2M HCl (aq) and EtOAc
  3. customThe organic layer was separated
  4. concentrationthen concentrated
  5. custompurified by the MDAP

Quellen und Nachweise

ORD-Eintrag
ord-d56a1162fb0d445f80f2087e70b8fe83
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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