Methylamine → 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N,5-dimethyl-1H-pyrazole-3-carboxamide

HRID 455045Notes

Reaction equation

HRID 455045 reaction equation
[CH3:1][NH:2]C(C1N(CC2N3C=C(C)C=CC3=NC=2C2C=CC(C)=CC=2)N=CN=1)=O.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:36]=[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]3[C:43]=2[CH2:44][N:45]2[C:49]([CH3:50])=[CH:48][C:47]([C:51](OC)=[O:52])=[N:46]2)=[CH:31][CH:30]=1.CN>>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[N:36]=[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]3[C:43]=2[CH2:44][N:45]2[C:49]([CH3:50])=[CH:48][C:47]([C:51]([NH:2][CH3:1])=[O:52])=[N:46]2)=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 670274852-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-2H-[1,2,4]triazole-3-carboxylic acid methylamideHCID 67028645methyl 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 670289161-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N,5-dimethyl-1H-pyrazole-3-carboxamide

Procedure

The title compound was prepared according to the procedure described for compound 68 from methyl 1-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-5-methyl-1H-pyrazole-3-carboxylate and methylamine. M/e+ 381 for C20H19ClN5O (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.20 (d, J=6.9 Hz, 1H), 7.68 m, 1H), 7.65 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.28 (m, 1H), 6.86 (td, J=6.9, 1.1 Hz, 1H), 6.62 (m, 1H), 6.52 (s, 1H), 5.64 (s, 2H), 2.93 (d, J=5.1 Hz, 3H), 1.99 (s, 3H) ppm.

Sources & evidence

ORD record
ord-1f0704b5b3c5469f88cff92ad144061a
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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