1-Butanol → 3,5-dimethyl-7-(1-methylethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester

HRID 371928Notes

Reaction equation

HRID 371928 reaction equation
[CH2:1]([OH:5])[CH2:2]CC.Cl[C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH3:18])[N:10]=[C:9]2[N:19]([CH3:22])[CH:20]=[N:21][C:8]=12.[CH2:23](N1C2=NC(C)=C(C(OCC)=O)C(Cl)=C2N=C1)CCC>CC(O)C>[CH2:16]([O:15][C:13]([C:12]1[C:7]([O:5][CH:1]([CH3:2])[CH3:23])=[C:8]2[N:21]=[CH:20][N:19]([CH3:22])[C:9]2=[N:10][C:11]=1[CH3:18])=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 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 571047483,5-dimethyl-7-(1-methylethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

When n-butyl alcohol is replaced by propane-2ol and 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester is processed as described for 3-butyl-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester in Example 5, 3,5-dimethyl-7-(1-methylethoxy)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester is obtained. Yield 67%, b.p. 170°-175°/0.01. The free acid is obtained as described in Example 9. The potassium salt is obtained by substituting potassium hydroxide for sodium hydroxide in that example.

Sources & evidence

ORD record
ord-ad5faf22866f4777a03cc36c27708a72
Source dataset
uspto-grants-1978_05
Patent number
US04088654

Reaction notes

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