Diisopropylethylamine → 4-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperazin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Piperazin-2-one	HCID 231360	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	1-(3-Chloro-4-fluorophenyl)-5-(5-methoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid	HCID 89602457	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperazin-2-one	HCID 86574308	—

Reaction Steps

0.06 ml (0.32 mmol) of N,N-diisopropylethylamine is added to a solution of 150 mg (0.16 mmol, 37% purity) of the compound of Example 64A, 32 mg (0.32 mmol) of 2-oxopiperazine, and 97 mg (0.26 mmol) of HATU in 5 ml of THF, and the mixture that is obtained is stirred for 20 hours at room temperature. After the further addition of 32 mg (0.32 mmol) of 2-oxopiperazine, stirring is continued for 5 hours at 60° C. The crude product is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). The title compound is obtained in a quantitative yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09296720B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-b415216b6a694a4eb80047419c316256
Source note	uspto-grants-2016_03