Dimethylformamide → 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide

HRID 2080276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080276
Cl[C:2]1[N:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:5].[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[CH2:23][CH2:24][NH2:25].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Cl:18][C:16]1[CH:15]=[CH:14][C:3]([C:4]([NH:6][CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:5])=[C:2]([NH:25][CH2:24][CH2:23][C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([F:19])[CH:21]=2)[N:17]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5339282-(3-Fluorophenyl)ethanamineHCID 175874832,6-dichloro-N-(pyridin-3-ylmethyl)pyridine-3-carboxamide

Produkt 1

HCID 597382236-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2,6-dichloro-N-(pyridin-3-ylmethyl)nicotinamide (20.4 g, 72.3 mmol), 3-fluorophenethyl amine (11.1 g, 79.5 mmol), K2CO3 (20 g 145 mmol) and DMF (200 mL) was stirred at 100° C. for 10 hours. The mixture was diluted with ethyl acetate (2×300 mL) and washed with saturated ammonium chloride, sodium bicarbonate and brine. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography to give 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (12.6 g, 46%). LRMS (M+H+) m/z 385.1.

Aufarbeitung

  1. washwashed with saturated ammonium chloride, sodium bicarbonate and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60903f7240f44134907988e09c2c190b
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932270B2

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