Riboflavin → HCID 178473777, Verbindung

HRID 1846810

Reaktionsgleichung

Reaktionsgleichung von HRID 1846810
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@@H:11]1[CH2:14][C@H:13]([O:15][C:16]2[C:21]([C:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:30])[CH3:29])[CH2:24][CH:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12]1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>C(O)C.[OH-].[Pd+2].[OH-].[Pd]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@@H:11]1[CH2:12][C@H:13]([O:15][C:16]2[C:21]([CH:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:30])[CH3:29])[CH2:26][CH2:27]3)=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:14]1

Komponenten

6

Edukt 2

HCID 493570RiboflavinHCID 178473776HCID 178473776, Verbindung

Produkt 1

HCID 178473777HCID 178473777, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.12 g, 0.28 mmol) in ethanol (2 mL) was added palladium hydroxide, 20 wt. % Pd (dry basis) on carbon, wet, Degussa type E101 NE/W (0.039 g, 0.056 mmol) and hydrogenated (double-walled balloon pressure) at 50° C. for 3 days. The cooled reaction was filtered via a pad of Celite®, and the filtrate was concentrated in vacuo and purified via flash column chromatography (20% EtOAc/Hexanes to 100% EtOAc) to afford 1-(4-(2-(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutoxy)pyridin-3-yl)piperidin-1-yl)ethanone as a white solid. [M+1]=423.0. IC50 (uM): 0.001566.

Aufarbeitung

  1. customThe cooled reaction
  2. filtrationwas filtered via a pad of Celite®
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified via flash column chromatography (20% EtOAc/Hexanes to 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7451cc8c84e042bba08cf220a5517de5
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952037B2

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