Cesium carbonate → HCID 178482883, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	(Z)-methyl 3-hydroxy-2-(pyrimidin-5-ylmethyl)acrylate	HCID 67774726	—
Reactant	N-[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]-N-methylguanidine	HCID 67776747	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 178482883	HCID 178482883	15.3%

Reaction Conditions

Temperature	130 °C

Reaction Steps

To the mixture of N-[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]-N-methylguanidine (50 mg, 0.106 mmol) and Cs2CO3 (138 mg, 0.425 mmol) in NMP (1 mL) was added methyl (2Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate (25 mg, 0.129 mmol). It was heated with a microwave reactor at 130° C. for 1 h. Purification via MDAP then afforded the title compound as a white solid (5 mg, 7.6%, yield). LCMS: rt=3.12 min, [M+H+]=502

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637536B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-eead891a7fb843c28834c08dd6048a28
Source note	uspto-grants-2014_01