ethyl 1H-imidazole-2-carboxylate → 1-[6-Chloro-2-(4-chloro-phenyl)-imidazo[1,2-a]pyridin-3-ylmethyl]-1H-imidazole-2-carboxylic acid ethyl ester

HRID 455020Notes

Reaction equation

HRID 455020 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]([CH2:42]Cl)=[C:33]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[N:34]=2)[CH:31]=1.[NH:44]1[CH:48]=[CH:47][N:46]=[C:45]1[C:49]([O:51][CH2:52][CH3:53])=[O:50]>>[CH2:52]([O:51][C:49]([C:45]1[N:44]([CH2:42][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:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[CH:48]=[CH:47][N:46]=1)=[O:50])[CH3:53]

Participants

4

Reactant 3

HCID 549404ethyl 1H-imidazole-2-carboxylateHCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridineHCID 67028658HCID 67028658, compound

Product 1

HCID 670289491-[6-Chloro-2-(4-chloro-phenyl)-imidazo[1,2-a]pyridin-3-ylmethyl]-1H-imidazole-2-carboxylic acid ethyl ester

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 1 from 6-chloro-3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride and ethyl 1H-imidazole-2-carboxylate. m/e+ 416 for C20H17Cl2N4O2 [M+H]+; 1H-NMR (300 MHz, CDCl3) δ 8.04 (dd, J=0.9, 6.3 Hz, 1H), 7.60 (m, 3H), 7.42 (dd, J=6.3, 8.1 Hz, 2H), 7.27 (m, 1H), 7.11 (m, 1H), 6.67 (dd, J=2.1, 3.3 Hz, 1H), 6.07 (d, J=2.1 Hz, 2H), 4.48 (q, J=7.2 Hz, 2H), 1.48 (t, J=7.2 Hz, 3H) ppm; 13C-NMR (75 MHz, CDCl3, δ) 160.222, 135.309, 130.815, 130.735, 129.653, 129.593, 127.897, 123.336, 123.283, 122.261, 121.647, 121.573, 118.475, 62.384, 53.016, 41.598, 41.544, 14.534 ppm.

Sources & evidence

ORD record
ord-6eb3b0658d7e494481198671cd87702f
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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