Benzoyl chloride → N-benzyl-2-(3-phenylpropanamido)-isonicotinamide

HRID 714316

Reaktionsgleichung

C(Cl)(=O)C1C=CC=CC=1.[C:10](Cl)(=[O:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:21][C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][N:37]=1)[C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>>[CH2:28]([NH:27][C:25](=[O:26])[C:24]1[CH:35]=[CH:36][N:37]=[C:22]([NH:21][C:10](=[O:19])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:23]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

Edukt 3

HCID 7412Benzoyl chloride

HCID 64801Benzenepropanoyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Produkt 1

HCID 67153848N-benzyl-2-(3-phenylpropanamido)-isonicotinamideAusbeute 42 %

Versuchsvorschrift

Following the procedure as describe in preparation of Example 5, making variations as required to replace benzoyl chloride with hydrocinnamoyl chloride, to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(3-phenylpropanamido)-isonicotinamide was obtained in 42% yield: mp 177-179° C.; 1H NMR (300 MHz, CDCl3) δ 10.63 (s, 1H), 9.26 (s, 1H), 8.46-8.36 (m, 2H), 7.54-7.14 (m, 11H), 4.43 (s, 2H), 2.86-2.68 (m, 4H); MS (ES+) m/z 360.6 (M+1).

Aufarbeitung

customas describe in preparation of Example 5

Quellen und Nachweise

ORD-Eintrag: ord-208b01bac54d41f5847bf631a0693001
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09187426B2

Verknüpfte Notizen

Wird geladen…