Sodium Hydroxide → (3,5-Bis-(4-methoxy-phenyl)-pyrazol-1-yl)-acetic acid

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	4-Chloro-6-(piperazin-1-yl)pyrimidine	HCID 16092266	—
Reactant	3-(4-Fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl acetic acid	HCID 86762671	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	(3,5-Bis-(4-methoxy-phenyl)-pyrazol-1-yl)-acetic acid	HCID 86762670	—

Reaction Steps

700 mg (3-(4-fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl)-acetic acid was dissolved in 10 mL DMF. 869 mg TBTU and 465 μL DIPEA were added to this solution and the mixture was stirred 1 min at RT. 448 mg 4-chloro-6-piperazine-1-yl-pyrimidine was added and stirring was continued for 2 h. Then 10 mL of a 1M NaOH solution and 50 mL CH2Cl2 were added, the organic phase was separated. The solvent was removed. The residue was dissolved in dichlormethane, water was added and the layers were separated. The organic layer was evaporated and the residue was purified by flash chromatography (silica gel, DCM/MeOH 0-30 to yield 500 mg of the desired compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08822464B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-9dd0692f9e734fd5ba2174a7f14de08b
Source note	uspto-grants-2014_09