1H-Benzimidazole-2-carboxamide, N-methyl- → 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N-methyl-1H-benzo[d]imidazole-2-carboxamide

HRID 455028Notes

Reaction equation

HRID 455028 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]=[CH:33][CH:34]=[CH:35][C:30]2=[N:29][C:28]=1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1.[CH3:43][NH:44][C:45]([C:47]1[NH:51][C:50]2[CH:52]=[CH:53][CH:54]=[CH:55][C:49]=2[N:48]=1)=[O:46]>>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C:28]2[N:29]=[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]3[C:27]=2[CH2:26][N:48]2[C:49]3[CH:55]=[CH:54][CH:53]=[CH:52][C:50]=3[N:51]=[C:47]2[C:45]([NH:44][CH3:43])=[O:46])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 99897391H-Benzimidazole-2-carboxamide, N-methyl-HCID 583370713-((1H-imidazol-1-yl)methyl)-6-methyl-2-p-tolylimidazo[1,2-a]pyridineHCID 670287193-(Chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 673068521-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N-methyl-1H-benzo[d]imidazole-2-carboxamide

Procedure

The title compound was prepared according to Method A and the experimentals described for compound 1 from 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine hydrochloride and N-methyl-1H-benzo[d]imidazole-2-carboxamide. M/e+ 416 for C23H19ClN5O (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.40 (d, J=6.9 Hz, 1H), 7.90 (d, J=4.7 Hz, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.62 (dd, J=13.1, 8.0 Hz, 2H), 7.51 (d, J=8.4 Hz, 2H), 7.18 (dd, J=8.4, 1.1 Hz, 2H), 6.98 (m, 1H), 6.73 (m, 1H), 6.67 (s, 2H) 3.12 (d, J=5.1 Hz, 3H) 1.83 (s, 1H) ppm.

Sources & evidence

ORD record
ord-08f029965d974067b1118ed98c13e53b
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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