Water → HCID 86661723, Verbindung

HRID 1020814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020814
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[OH:13][CH2:14][CH2:15][CH2:16][C:17]1([OH:20])[CH2:19][CH2:18]1.C(O[K])(C)(C)C.O>CN(C=O)C>[Cl:12][C:8]1[C:9]([Cl:11])=[N:10][C:2]([O:13][CH2:14][CH2:15][CH2:16][C:17]2([OH:20])[CH2:19][CH2:18]2)=[C:3]([CH:7]=1)[C:4]([NH2:6])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10582773HCID 10582773, VerbindungHCID 537509302,5,6-Trichloropyridine-3-carboxamideHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 86661723HCID 86661723, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of compound 2,5,6-trichloronicotinamide (0.6 g, 2.7 mmol), 1-(3-hydroxypropyl)cyclopropanol (370 mg, 3.2 mmol) and tert-BuOK (363 mg, 3.2 mmol) in DMF was stirred at room temperature overnight and the reaction mixture was then poured into cold water, the mixture was extracted twice with ethyl acetate, the combined organic layers were washed with brine twice, dried over Na2SO4 and concentrated, the residue was purified by column chromatography (silica gel, Petroleum ether:EtOAc=1:0 to 5:1) to give the 5,6-dichloro-2-(3-(1-hydroxycyclopropyl)propoxy)nicotinamide (0.72 g, 73%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.65 (s, 1H), 8.29 (s, 1H), 8.03 (s, 1H), 5.48 (s, 1H), 4.82 (t, 2H, J=6.4 Hz), 2.36 (m, 2H), 1.97 (m, 2H), 0.94 (t, 2H), 0.73 (t, 2H).

Aufarbeitung

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washthe combined organic layers were washed with brine twice
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (silica gel, Petroleum ether:EtOAc=1:0 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-e88578d948a344f78c0cd0c7bc435f42
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716478B2

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