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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1897406Generated: October 26, 2026

1,1'-Carbonyldiimidazole → 1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-n-[2-[(phenylmethyl)amino]ethyl]-

https://huagongshe.com/reaction/1897406

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
ReactantN-BenzylethylenediamineHCID 77801—
Reactant1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-HCID 57418739—
SolventTetrahydrofuranHCID 8028—
Product1h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-n-[2-[(phenylmethyl)amino]ethyl]-HCID 42611124100%

Reaction Steps

A solution of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (compound 10g, prepared as described in Example 46) in THF was treated with carbonyldiimidazole (1.2 equivalents) at room temperature under nitrogen atmosphere. After stirring at for 18 hours, the reaction was treated with N1-benzyl-ethane-1,2-diamine (1 equivalent). After an additional 18 hours, the solvent was allowed to slowly evaporate and the residue was purified in a Sep Pak cartridge eluting with a gradient of 100% CH2Cl2 to MeOH/CH2Cl2 to provide compound 11g-5 as an oil in 100% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08518983B2
Source datasetuspto-grants-2013_08
ORD IDord-65e1676279d1436fbef145d3f6e99781
Source noteuspto-grants-2013_08