Hydrochloric Acid → 3-(2-chloro-4-(1-propoxy)benzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid

HRID 1368235Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH3:27])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:15]([O:17]C)=[O:16])=[CH:12][C:13]([CH3:14])=[C:8]2[N:7]=[C:6]1[CH3:19].[OH-].[Na+].Cl.O>O1CCOCC1>[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH3:27])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:15]([OH:17])=[O:16])=[CH:12][C:13]([CH3:14])=[C:8]2[N:7]=[C:6]1[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of methyl 3-(2-chloro-4-(1-propoxy)benzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (475 mg) in 1,4-dioxane was added 1N aqueous sodium hydroxide solution, and the mixture was heated to 60° C. and stirred for 30 min. It was air cooled and adjusted to pH 4 by dropwise addition of 1N hydrochloric acid. Water (25 ml) was added and the mixture was stirred at room temperature. The precipitated crystals were collected by filtration and dried under reduced pressure at 60° C. Thereto was added acetonitrile (3 ml) and the mixture was heated and stirred at room temperature. The crystals were collected by filtration and dried under reduced pressure at 60° C. to give 3-(2-chloro-4-(1-propoxy)benzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid as thin yellow crystals (426 mg).

Workup

temperaturecooled
stirringthe mixture was stirred at room temperature
filtrationThe precipitated crystals were collected by filtration
customdried under reduced pressure at 60° C
additionThereto was added acetonitrile (3 ml)
temperaturethe mixture was heated
stirringstirred at room temperature
filtrationThe crystals were collected by filtration
customdried under reduced pressure at 60° C.

Sources & evidence

ORD record: ord-a9d342aacc654973aab586f0d6154e3c
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573274B1

Reaction notes

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