2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamide → 2-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carbonitrile

HRID 1882404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882404
FC1C=CC(CN2C(=O)N(C3SC(C(N)=O)=C(C)N=3)C=N2)=CC=1.[F:24][C:25]1[CH:46]=[CH:45][C:28]([CH2:29][N:30]2[CH2:34][CH2:33][N:32]([C:35]3[S:36][C:37]([C:41]([NH2:43])=O)=[C:38]([CH3:40])[N:39]=3)[C:31]2=[O:44])=[CH:27][CH:26]=1>>[F:24][C:25]1[CH:46]=[CH:45][C:28]([CH2:29][N:30]2[CH2:34][CH2:33][N:32]([C:35]3[S:36][C:37]([C:41]#[N:43])=[C:38]([CH3:40])[N:39]=3)[C:31]2=[O:44])=[CH:27][CH:26]=1

Komponenten

3

Edukt 2

HCID 441936012-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamideHCID 580314432-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

Produkt 1

HCID 579197612-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carbonitrileAusbeute 68 %

Versuchsvorschrift

Following the procedure as describe in Preparation 20, making variations as required to replace 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxamide with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a pale yellow solid in 68% yield: mp 136-139° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.35-7.31 (m, 2H), 7.18-7.13 (m, 2H), 4.41 (s, 2H), 4.00 (t, J=6.0 Hz, 2H), 3.46 (t, J=6.0 Hz, 2H) 2.37 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.1 (d), 161.4, 161.1, 155.3, 150.3, 132.8 (d), 130.5 (d), 115.9 (d), 114.4, 92.4, 46.6, 42.7, 42.3, 17.3; MS (ES+) m/z 317.9 (M+1).

Aufarbeitung

  1. customas describe in Preparation 20

Quellen und Nachweise

ORD-Eintrag
ord-c25839e3a7db4d0285fd393ba8028b4d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318949B2

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