methyl 1H-1,2,4-triazole-3-carboxylate → Methyl 1-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1H-1,2,4-triazole-5-carboxylate

HRID 455033Notes

Reaction equation

HRID 455033 reaction equation
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]([F:36])[CH:34]=[CH:35][C:30]2=[N:29][C:28]=1[C:37]1[CH:42]=[CH:41][C:40]([F: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>>[F:36][C:33]1[CH:34]=[CH:35][C:30]2[N:31]([C:27]([CH2:26][N:44]3[C:48]([C:49]([O:51][CH3:52])=[O:50])=[N:47][CH:46]=[N:45]3)=[C:28]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[N:29]=2)[CH:32]=1

Participants

4

Reactant 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 670302703-(Chloromethyl)-6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 67028848Methyl 1-((6-fluoro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-1H-1,2,4-triazole-5-carboxylate

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 1 from 3-(chloromethyl)-6-fluoro-2-(4-fluorophenyl)imidazo[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). m/e− 370 for C18H14F2N5O2 (M+H)−.

Workup

  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)

Sources & evidence

ORD record
ord-213f1172002d4d4883a636b25d45af4c
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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