Hydrochloric Acid → 6-(4-Hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2079544Notes

Reaction equation

COCCOC[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20]#[N:21])[C:17]3[N:22]=[CH:23][N:24]([CH3:25])[C:16]=3[CH:15]=2)=[CH:10][C:9]=1[C:26]([F:29])([F:28])[F:27].Cl.[Cl-].[Na+]>C1COCC1>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[C:18]([C:20]#[N:21])[C:17]3[N:22]=[CH:23][N:24]([CH3:25])[C:16]=3[CH:15]=2)=[CH:10][C:9]=1[C:26]([F:29])([F:28])[F:27]

Participants

Conditions

Temperature: 65 °C

Procedure

6-(4-(2-Methoxy-ethoxymethoxy)-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (7.5 g) was added to a mixed solvent of THF (300 ml) and 1M HCl (aq). The mixture was heated to 65° C. until the full disappearance of all starting material. After adding saturated sodium chloride solution (200 ml), the mixture was extracted with ethyl acetate (300 ml×3), and the combined organic layers were then dried over sodium sulphate, solvent was removed under reduces pressure, and the residue was triturated in ether. Product, 6-(4-hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (5.9 g) was collected by filtration.

Workup

extractionthe mixture was extracted with ethyl acetate (300 ml×3)
dry with materialthe combined organic layers were then dried over sodium sulphate, solvent
customwas removed
customthe residue was triturated in ether
filtrationProduct, 6-(4-hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (5.9 g) was collected by filtration

Sources & evidence

ORD record: ord-7b1eea1a9be94d558987e9ebd44847ab
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932251B2

Reaction notes

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