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

HRID 714314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714314
C(Cl)(=O)C1C=CC=CC=1.[F:10][C:11]([F:23])([F:22])[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.[NH2:24][C:25]1[CH:26]=[C:27]([CH:38]=[CH:39][N:40]=1)[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>>[CH2:31]([NH:30][C:28](=[O:29])[C:27]1[CH:38]=[CH:39][N:40]=[C:25]([NH:24][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([O:12][C:11]([F:23])([F:22])[F:10])=[CH:14][CH:15]=2)[CH:26]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

4

Edukt 3

HCID 7412Benzoyl chlorideHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 187528972-amino-N-benzylisonicotinamide

Produkt 1

HCID 67153805N-benzyl-2-(4-trifluoromethoxybenzoylamino)isonicotinamideAusbeute 6 %

Versuchsvorschrift

Following the procedure as describe in preparation of Example 5, making variations as required to replace benzoyl chloride with 4-(trifluoromethoxy)benzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(4-trifluoromethoxybenzoylamino)isonicotinamide was obtained in 6% yield: mp 151-153° C.; 1H NMR (300 MHz, CDCl3) δ 8.83 (br s, 1H), 8.68 (s, 1H), 8.35 (d, J=5.0 Hz, 1H), 7.93 (d, J=9.0 Hz, 2H), 7.58-7.54 (m, 1H), 7.38-7.28 (m, 7H), 6.75 (br s, 1H), 4.64 (d, J=5.7 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ 165.1, 164.5, 152.2, 151.8, 148.9, 144.2, 137.4, 132.0, 129.1, 128.8, 128.0, 127.8, 121.9, 120.8, 118.7, 118.5, 115.1, 110.5, 44.2; MS (ES+) m/z 416.4 (M+1).

Aufarbeitung

  1. customas describe in preparation of Example 5

Quellen und Nachweise

ORD-Eintrag
ord-59ce089877de469c87ce0a29a38f62da
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187426B2

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