3-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester → 7-butoxy-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 371927Notes

Reaction equation

HRID 371927 reaction equation
[CH2:1]([N:5]1[C:9]2=[N:10][C:11]([CH3:20])=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13](Cl)=[C:8]2[N:7]=[CH:6]1)CCC.ClC1[C:27]([C:28](OCC)=[O:29])=[C:26]([CH3:33])N=C2N(C)C=NC=12>>[CH2:28]([O:29][C:13]1[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([CH3:20])[N:10]=[C:9]2[N:5]([CH3:1])[CH:6]=[N:7][C:8]=12)[CH2:27][CH2:26][CH3:33]

Participants

3

Reactant 2

HCID 123876393-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl esterHCID 123876407-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 867344207-butoxy-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl esterYield 61%

Procedure

By replacing 3-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester in Example 5 with 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester of Example 2 c, 7-butoxy-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester is formed. Yield 61%, b.p. 180°-190°/0.01.

Sources & evidence

ORD record
ord-00b49bb6f01940ef960efa0da37614c9
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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