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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 18614Generated: October 30, 2026

5-Fluoro-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid ethyl ester → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-fluoro-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid

https://huagongshe.com/reaction/18614

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Fluoro-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid ethyl esterHCID 68616561—
Reactant5-(5-Chlorothiophen-2-yl)isoxazol-3-ylmethyl methanesulfonateHCID 86595878—
Product1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-fluoro-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acidHCID 67012529—

Reaction Steps

1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-fluoro-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid was prepared by a procedure according to example 81 starting from 230 mg (0.60 mmol) 5-Fluoro-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid ethyl ester and 179.5 mg (0.60 mmol) methanesulfonic acid 5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl ester. Hydrolysis of the resulting ethyl ester by treatment with LiOH and purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave the title compound as its formiate in form of a white amorphous solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07741341B2
Source datasetuspto-grants-2010_06
ORD IDord-4daa0075bca94a34a3f4101fea6a7eff
Source noteuspto-grants-2010_06