2-Fluorobenzoyl chloride → N-benzyl-2-(2-chloro-5-fluorobenzamido)-isonicotinamide

HRID 714326

Reaktionsgleichung

Reaktionsgleichung von HRID 714326
FC1C=CC=CC=1C(Cl)=O.[Cl:11][C:12]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:13]=1[C:14](Cl)=[O:15].[NH2:22][C:23]1[CH:24]=[C:25]([CH:36]=[CH:37][N:38]=1)[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>>[CH2:29]([NH:28][C:26](=[O:27])[C:25]1[CH:36]=[CH:37][N:38]=[C:23]([NH:22][C:14](=[O:15])[C:13]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:12]=2[Cl:11])[CH:24]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

4

Edukt 3

HCID 98082-Fluorobenzoyl chlorideHCID 27575402-Chloro-5-fluorobenzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Produkt 1

HCID 67153861N-benzyl-2-(2-chloro-5-fluorobenzamido)-isonicotinamideAusbeute 57 %

Versuchsvorschrift

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 2-chloro-5-fluorobenzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(2-chloro-5-fluorobenzamido)-isonicotinamide was obtained as a colorless solid in 57% yield: mp 180-181° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) (9.15 (d, J=13.8 Hz, 1H), 8.60 (s, 1H), 8.44 (d, J=5.0 Hz, 1H), 8.07 (dd, J=6.6, 2.8 Hz, 1H), 7.58 (d, J=4.2 Hz, 1H), 7.52-7.46 (m, 1H), 7.36-7.12 (m, 6H), 6.67 (s, 1H), 4.65 (d, J=5.7 Hz, 2H); MS (ES+) m/z 384.5 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-fb9f943c7dd14938acd91ebcf4fe7291
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187426B2

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