1,3-Cyclohexanediol → (3-hydroxycyclohexyl) 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

HRID 402703

Reaktionsgleichung

Reaktionsgleichung von HRID 402703
[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:26][CH2:27][CH3:28])=[O:25])[C:12]2=[O:29])=[CH:2]1.[CH:30]1(O)[CH2:35]CC[CH:32]([OH:36])[CH2:31]1>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:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[C:13]([C:24]([O:26][CH:27]3[CH2:35][CH2:30][CH2:31][CH:32]([OH:36])[CH2:28]3)=[O:25])[C:12]2=[O:29])=[CH:2]1

Komponenten

5

Edukt 2

HCID 104331,3-CyclohexanediolHCID 178469558ethyl 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

Produkt 1

HCID 178524383(3-hydroxycyclohexyl) 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylateAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of the compound (0.10 g, 0.25 mmol) of Example 21, 1,3-cyclohexanediol (0.44 g, 3.8 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.018 g, 0.019 mmol) in N,N-dimethylacetamide (1.0 mL) was stirred at 130° C. for 1.5 days. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.010 g, y. 13%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-aa96d85647734d7882ecbe0903cc6797
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742113B2

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