3-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine → 1-(6-Chloro-2-phenyl-imidazo[1,2-a]pyridin-3-ylmethyl)-1H-[1,2,4]triazole-3-carboxylic acid methyl ester

HRID 455032Notes

Reaction equation

HRID 455032 reaction equation
N1(CC2N3C=C(C)C=CC3=NC=2C2C=CC(C)=CC=2)C=CN=C1.Cl.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([CH2:41]Cl)=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:34]=2)[CH:31]=1.[NH:43]1[CH:47]=[N:46][C:45]([C:48]([O:50][CH3:51])=[O:49])=[N:44]1>>[CH3:51][O:50][C:48]([C:45]1[N:46]=[CH:47][N:43]([CH2:41][C:32]2[N:30]3[CH:31]=[C:26]([Cl:25])[CH:27]=[CH:28][C:29]3=[N:34][C:33]=2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:44]=1)=[O:49]

Participants

4

Reactant 3

HCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridineHCID 670287296-Chloro-3-(chloromethyl)-2-phenylimidazo[1,2-a]pyridine hydrochlorideHCID 178499122HCID 178499122, compound

Product 1

HCID 673067201-(6-Chloro-2-phenyl-imidazo[1,2-a]pyridin-3-ylmethyl)-1H-[1,2,4]triazole-3-carboxylic acid methyl ester

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 1 from 6-chloro-3-(chloromethyl)-2-phenylimidazo[1,2-a]pyridine hydrochloride and methyl 1H-1,2,4-triazole-3-carboxylate. The two isomers were separated by silica gel chromatography (eluted with 20% acetone/hexane to flush out the less polar isomer (44) and then flashed with 50% acetone to get the second compound off the column (45). Compound 44: m/e+ 368 for C18H15ClN5O2 [M+H]−; 1H-NMR (400 MHz, CDCl3) δ 8.35 (d, J=1.1 Hz, 1H), 7.98 (s, 1H), 7.76 (dd, J=1.4, 8.0 Hz, 2H), 7.61 (d, J=9.5 Hz, 1H), 7.42 (m, 3H), 7.24 (m, 1H), 6.17 (s, 2H), 3.97 (s, 3H) ppm; Compound 45: m/e+ 368 for C18H15ClN5O2 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 8.18 (d, J=1.1 Hz, 1H), 7.99 (s, 1H), 7.63 (m, 3H), 7.44 (m, 3H), 7.25 (m, 1H), 5.82 (s, 2H), 3.97 (s, 3H) ppm.

Workup

  1. customThe title compound was prepared
  2. customThe two isomers were separated by silica gel chromatography (
  3. washeluted with 20% acetone/hexane
  4. customto flush out the less polar isomer (44)

Sources & evidence

ORD record
ord-c350602ac25447f1870588146f75b407
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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