Triethylamine → 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide

HRID 1053154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053154
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:36][O:37][C:38]1[CH:43]=[C:42]([NH2:44])[CH:41]=[CH:40][N:39]=1.CCN(CC)CC>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:44][C:42]1[CH:41]=[CH:40][N:39]=[C:38]([O:37][CH3:36])[CH:43]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2808912-Methoxypyridin-4-amineHCID 27365375-Chloro-2-fluorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 867284685-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamideAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-chloro-2-fluoro-benzoic acid (5.0 g, 28.64 mmol), HATU (10.89 g, 28.64 mmol), 2-methoxypyridin-4-amine (3.6 g, 28.64 mmol) and Et3N (15.98 mL, 114.60 mmol) in dichloromethane (45.0 mL) was stirred at room temperature overnight. The crude mixture was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes (0-50%) to yield 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (3.8 g, 47%) as a white solid. ESI-MS m/z calc. 280.04. found 281.3 (M+1)+; Retention time: 1.31 minutes (3 minutes run).

Aufarbeitung

  1. customThe crude mixture was purified by column chromatography
  2. washeluting with a gradient of ethyl acetate in hexanes (0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-77c47faf3a134507b99b46f72af6131c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393235B2

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