Hydrochloric Acid → 6-(2-((Dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1481707Notes

Reaction equation

HRID 1481707 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:6]=[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:22]([CH2:23][CH3:24])=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[C:15]([O:25]C)[N:14]=3)=[CH:9][N:8]2[CH:27]=1)[CH3:3].Cl>>[CH3:3][N:2]([CH2:4][C:5]1[N:6]=[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:14][C:15](=[O:25])[C:16]([C:17]([OH:19])=[O:18])=[CH:21][C:22]=3[CH2:23][CH3:24])=[CH:9][N:8]2[CH:27]=1)[CH3:1]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 71284140Methyl 6-(2-((dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinate

Product 1

HCID 712848136-(2-((Dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 123.3%

Procedure

Methyl 6-(2-((dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinate (100.6 mg, 0.27 mmol) was heated with 6 M HCl (1.50 mL) at 80° C. for 3 h. HCl was removed under reduced pressure affording 6-(2-((dimethylamino)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (113.3 mg) as dihydrochloride salt in 99% overall yield.

Workup

  1. customHCl was removed under reduced pressure

Sources & evidence

ORD record
ord-850f19fd971841a1b4808cdb65d2dc9a
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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