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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 551906Generated: October 26, 2026

Dimethylformamide → Methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(4-cyanoanilino)-carbonyl]amino}methyl)phenoxy]acetate

https://huagongshe.com/reaction/551906

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantTris(hydroxymethyl)aminomethaneHCID 6503—
Reactant4-Cyanophenyl isocyanateHCID 170380—
ReactantMethyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}acetateHCID 57554567—
SolventDichloromethaneHCID 6344—
ProductMethyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(4-cyanoanilino)-carbonyl]amino}methyl)phenoxy]acetateHCID 11621237132.1%

Reaction Steps

To a solution of methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]-phenoxy}acetate (37 mg, 0.084 mmol) in anhydrous DCM (2 ml) was added 4-cyanophenyl isocyanate (Aldrich, 45 mg, 0.31 mmol) and the reaction mixture was stirred at rt for 18 hrs. Then PS-trisamine resin (75 mg, Novabiochem, 3.5 mmol/g) and DMF (1 mL) were added and the resulting mixture was stirred at rt for 5 additional hrs. Removal of the resin by filtration followed by evaporation of the solvents gave 65 mg (97%) of the title compound as a pale yellow oil. HPLC, Rt: 5.7 min (purity: 74.1%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07947851B2
Source datasetuspto-grants-2011_05
ORD IDord-b7fb90f33d7946b995f6784ce9ebb79e
Source noteuspto-grants-2011_05