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2-Aminothiazole → HCID 86649623, Verbindung

HRID 1897935
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1897935
Cl[C:2]1[N:7]=[C:6]([CH2:8][C:9]2([OH:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[OH:22][C:9]1([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH:23][C:24]3[S:25][CH:26]=[CH:27][N:28]=3)[N:7]=2)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)2×HCID 57366393HCID 57366393, Verbindung

Produkt 1

HCID 86649623
HCID 86649623, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysator2×HCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 50.3 mg of tert-butyl 4((6-chloropyridin-2-yl)methyl)-4-hydroxypiperidine-1-carboxylate, 19.3 mg of 2-aminothiazole, 9.0 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 4.8 mg of bis(dibenzylideneacetone)palladium(0), 25.2 mg of sodium carbonate and 0.77 ml of toluene was stirred at 100° C. overnight and 120° C. overnight. 156.6 mg of cesium carbonate, 94.4 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and 47.1 mg of bis(dibenzylideneacetone)palladium(0) were added to the reaction mixture, followed by stirring the reaction mixture at 130° C. overnight. The reaction mixture was cooled to room temperature, and diluted with chloroform. An insoluble matter was filtered off using Celite, and the filtrate was concentrated in vacuo. The resulting residue was purified by a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=10/1) to give the title compound as a brown oil.

Aufarbeitung

  1. stirringby stirring the reaction mixture at 130° C. overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationAn insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck), chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-114a40bf5c464761b5cae7ac4fc4ed1a
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08519136B2

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