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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43604Generated: October 28, 2026

Thionyl Chloride → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate

https://huagongshe.com/reaction/43604

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant4-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67548929—
ReactantEthyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylateHCID 86648577—
ProductEthyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylateHCID 8664857959.5%

Reaction Steps

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.13 g, 0.75 mmol), thionyl chloride (2 mL) and ethyl cis(±)-2-(4-amino-3-methoxypiperidin-1-yl)-1,3-oxazole-4-carboxylate obtained in Example (103d) (0.3 g, 1.12 mmol). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=4/1, 1/0) gave 0.19 g of the title compound as a brown oily substance (60%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536197B2
Source datasetuspto-grants-2013_09
ORD IDord-455df27106854f048040999cd490f210
Source noteuspto-grants-2013_09