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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 392981Generated: October 30, 2026

Methyl 6-(cyclohexylamino)-5-nitronicotinate → Methyl 3-cyclohexyl-2-(4-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate

https://huagongshe.com/reaction/392981

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 6-(cyclohexylamino)-5-nitronicotinateHCID 22660792—
ReactantEthyl 4-hydroxybenzimidate hydrochlorideHCID 135442973—
SolventMethanolHCID 887—
ProductMethyl 3-cyclohexyl-2-(4-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylateHCID 13567409388%

Reaction Steps

A solution of intermediate 58 (5.0 g, 20.0 mmol) and ethyl 4-hydroxybenzimidate hydrochloride (6.0 g, 30.0 mmol) in methanol (67 mL) was heated at reflux for 22 h. The reaction mixture was then cooled to rt and the precipitated solid was collected by vacuum filtration and washed sparingly with cold methanol to afford intermediate 59 as a white solid (6.13 g, 88%). ESI-MS m/e 352.2 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06803374B2
Source datasetuspto-grants-2004_10
ORD IDord-fb0db238a1b8436e86c5242a3d404d20
Source noteuspto-grants-2004_10