methyl 1H-1,2,4-triazole-3-carboxylate → 1-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-1H-[1,2,4]triazole-3-carboxylic acid methyl ester

HRID 455018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455018
N1(CC2N3C=C(C)C=CC3=NC=2C2C=CC(C)=CC=2)C=CN=C1.Cl.Cl[CH2:26][C:27]1[N:31]2[CH:32]=[C:33]([CH3:36])[CH:34]=[CH:35][C:30]2=[N:29][C:28]=1[C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1.[NH:44]1[C:48]([C:49]([O:51][CH3:52])=[O:50])=[N:47][CH:46]=[N:45]1>>[CH3:52][O:51][C:49]([C:48]1[N:47]=[CH:46][N:45]([CH2:26][C:27]2[N:31]3[CH:32]=[C:33]([CH3:36])[CH:34]=[CH:35][C:30]3=[N:29][C:28]=2[C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[N:44]=1)=[O:50]

Komponenten

4

Edukt 3

HCID 2735089methyl 1H-1,2,4-triazole-3-carboxylateHCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridineHCID 670287243-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride

Produkt 1

HCID 670287531-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-1H-[1,2,4]triazole-3-carboxylic acid methyl ester

Versuchsvorschrift

The title compound was prepared according to Method A and the experimentals described for compound 1 from 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and methyl 1H-1,2,4-triazole-5-carboxylate. The two isomers were separated by silica gel chromatography eluted with 20% acetone to flash out the less polar spot and 50% acetone to flash out the second spot (more polar spot). Compound 10: m/e+ 362 for C20H20N5O2 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 7.95 (s, 2H), 7.65 (d, J=8.0 Hz, 2H), 7.56 (d, J=9.1 Hz, 1H), 7.23 (d, J=8.0 Hz, 2H), 7.10 (dd, J=1.4, 9.1 Hz, 1H), 6.15 (s, 2H), 3.98 (s, 3H), 2.38 (s, 3H), 2.31 (s, 3H) ppm; Compound 11: m/e+ 362 for C20H20N5O2 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 7.74 (s, 1H), 7.58 (d, J=9.5 Hz, 1H), 7.54 (d, J=7.7 Hz, 2H), 7.24 (d, J=7.7 Hz, 2H), 7.14 (d, J=9.5 Hz, 1H), 5.81 (s, 2H), 3.98 (s, 3H), 2.37 (s, 3H), 2.29 (s, 3H) ppm.

Aufarbeitung

  1. customThe two isomers were separated by silica gel chromatography
  2. washeluted with 20% acetone to flash out the less polar spot and 50% acetone to flash out the second spot (more polar spot)

Quellen und Nachweise

ORD-Eintrag
ord-23844c0091684a60bec6cc7e753f0fc7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497278B2

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