3-Thiophenecarboxylic acid, ethyl ester → 8-Chloro-3-pentyl-1-{4-[5-(3-thienyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097695
[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][C:33]([C:36](OCC)=O)=[CH:32]1>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:33]4[CH:34]=[CH:35][S:31][CH:32]=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 798243-Thiophenecarboxylic acid, ethyl esterHCID 2723922Sodium ethoxideHCID 178506473HCID 178506473, Verbindung

Produkt 1

HCID 593956078-Chloro-3-pentyl-1-{4-[5-(3-thienyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °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 ml) was treated with a 21% solution of NaOEt in EtOH (55 μl, 0.21 mmol) and ethyl 3-thiophenecarboxylate (18 μl, 0.13 mmol). The mixture was heated in the microwave at 150° C. for 10 min. After cooling, the reaction was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated and the aqueous extracted again with EtOAc. The combined extracts were concentrated and purified by the MDAP. The title compound was obtained as an off-white solid (20 mg, 32%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between 2M HCl (aq) and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous extracted again with EtOAc
  5. concentrationThe combined extracts were concentrated
  6. custompurified by the MDAP

Quellen und Nachweise

ORD-Eintrag
ord-79c4f2cb49bf45c89429cd0927aaf578
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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