(1R,2S)-cyclopentane-1,2-diol → HCID 178525690, Verbindung

HRID 402699

Reaktionsgleichung

Reaktionsgleichung von HRID 402699
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:13]([C:24](OCC)=[O:25])[C:12]2=[O:29])=[CH:2]1.[C@@H:30]1([OH:36])[CH2:34][CH2:33][CH2:32][C@@H:31]1[OH:35]>CN(C)C(=O)C.[Zn]>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:13]([C:24]([O:35][C@@H:31]3[CH2:32][CH2:33][CH2:34][C@@H:30]3[OH:36])=[O:25])[C:12]2=[O:29])=[CH:2]1

Komponenten

5

Edukt 2

HCID 2733293(1R,2S)-cyclopentane-1,2-diolHCID 178469558ethyl 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

Produkt 1

HCID 178525690HCID 178525690, VerbindungAusbeute 22,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of the compound (0.10 g, 0.25 mmol) of Example 21, (1R,2S)-1,2-cyclopentanediol (0.26 g, 2.5 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.012 g, 0.012 mmol) in N,N-dimethylacetamide (1.5 mL) was stirred with the microwave synthesizer (Biotage Initiator™) at 130° C. for 2 h. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.025 g, y. 20%).

Aufarbeitung

  1. customthe precipitate was removed by filtration
  2. customThe filtrate was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-521643bdef9249118426ca0270b8f8d6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742113B2

Verknüpfte Notizen

Wird geladen…