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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1746775Generated: October 27, 2026

Diisopropylamine → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(4-{[(2-methoxyethyl)amino]sulfonyl}-2-methylphenyl)pyrimidine-4-carboxamide

https://huagongshe.com/reaction/1746775

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylamineHCID 7912—
ReactantN-(cyclopropylmethyl)cyclohexanamineHCID 1531432—
Reactant6-chloro-N-(4-(N-(2-methoxyethyl)sulfamoyl)-2-methylphenyl)pyrimidine-4-carboxamideHCID 59447107—
SolventEthanolHCID 702—
Product6-[cyclohexyl(cyclopropylmethyl)amino]-N-(4-{[(2-methoxyethyl)amino]sulfonyl}-2-methylphenyl)pyrimidine-4-carboxamideHCID 5944697184.3%

Reaction Conditions

Temperature160 °C

Reaction Steps

A solution of 6-chloro-N-(4-(N-(2-methoxyethyl)sulfamoyl)-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 38, 100 mg; 0.26 mmol) and diisopropylamine (91 mL; 0.52 mmol) in ethanol (2.5 ml) was treated with N-(cyclopropylmethyl)cyclohexanamine (54.4 mg; 0.33 mmol). The mixture was heated to 160° C. in a microwave for 1 hour and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as a white solid (110 mg, 84%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09150519B2
Source datasetuspto-grants-2015_10
ORD IDord-94868dfe55ed44e29d4a03c3b6f1d15f
Source noteuspto-grants-2015_10