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

HRID 455019Notes

Reaction equation

HRID 455019 reaction equation
[N:1]1([CH2:6][C:7]2[N:11]3[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.ClCC1N2C=C(C)C=CC2=NC=1C1C=CC(C)=CC=1.N1C=CN=C1[C:49]([O:51][CH2:52][CH3:53])=[O:50]>>[CH2:52]([O:51][C:49]([C:2]1[N:1]([CH2:6][C:7]2[N:11]3[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]3=[N:9][C:8]=2[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=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 670287243-(Chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 670286731-(6-Methyl-2-p-tolyl-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 3-(chloromethyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridine hydrochloride and ethyl 1H-imidazole-2-carboxylate. m/e+ 375 for C22H23N4O2 [M+H]+; 1H-NMR (300 MHz, CDCl3) δ 7.63 (m, 4H), 7.24 (m, 4H), 6.73 (d, J=0.9 Hz, 1H), 6.07 (s, 2H), 4.39 (m, 2H), 2.39 (s, 3H), 2.29 (s, 3H), 1.43 (m, 3H) ppm.

Sources & evidence

ORD record
ord-2ae8a64d12734043bfbcf62127de7714
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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