5-Amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester → 3-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 371923Notes

Reaction equation

HRID 371923 reaction equation
N[C:2]1C(Cl)=C(C(OCC)=O)C(C)=NC=1NCC.[NH2:18][C:19]1[C:20]([Cl:36])=[C:21]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:22]([CH3:30])=[N:23][C:24]=1[NH:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[CH2:26]([N:25]1[C:24]2=[N:23][C:22]([CH3:30])=[C:21]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:20]([Cl:36])=[C:19]2[N:18]=[CH:2]1)[CH2:27][CH2:28][CH3:29]

Participants

3

Reactant 2

HCID 123876185-Amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl esterHCID 123876195-Amino-6-butylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester

Product 1

HCID 123876393-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl esterYield 83%

Procedure

By replacing 5-amino-6-ethylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester in Example 1 d with 5-amino-6-butylamino-4-chloro-2-methylpyridine-3-carboxylic acid, ethyl ester, 3-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester is obtained. Yield 83%, b.p. 190°-200°/0.01.

Workup

  1. customin Example 1 d

Sources & evidence

ORD record
ord-e08218d3d8a743cdb6c3156e971aecb5
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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