Benzoyl chloride → N-benzyl-2-(4-trifluoromethylbenzoylamino)-isonicotinamide

HRID 714315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714315
C(Cl)(=O)C1C=CC=CC=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.[NH2:23][C:24]1[CH:25]=[C:26]([CH:37]=[CH:38][N:39]=1)[C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>>[CH2:30]([NH:29][C:27](=[O:28])[C:26]1[CH:37]=[CH:38][N:39]=[C:24]([NH:23][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=2)[CH:25]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

4

Edukt 3

HCID 7412Benzoyl chlorideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamide

Produkt 1

HCID 67153835N-benzyl-2-(4-trifluoromethylbenzoylamino)-isonicotinamideAusbeute 60 %

Versuchsvorschrift

Following the procedure as describe in preparation of Example 5, variations as required to replace benzoyl chloride with 4-(trifluoromethy)benzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(4-trifluoromethylbenzoylamino)-isonicotinamide was obtained in 60% yield: mp 181-183° C.; 1H NMR (300 MHz, CDCl3) δ 8.92 (br s, 1H), 8.61 (s, 1H), 8.32 (d, J=4.3 Hz, 1H), 7.97 (d, J=7.8 Hz, 2H), 7.73 (d, J=7.8 Hz, 2H), 7.53 (d, J=4.3 Hz, 1H), 7.38-7.15 (m, 5H), 6.98 (br s, 1H), 4.63 (d, J=5.7 Hz, 2H); MS (ES+) m/z 400.4 (M+1).

Aufarbeitung

  1. customas describe in preparation of Example 5, variations

Quellen und Nachweise

ORD-Eintrag
ord-de6cc7c7c0ee48e1bc0e2667e3d188eb
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187426B2

Notizen zur Reaktion

Wird geladen…