4-Methylmorpholine → (E)-4-ethoxyacetyl-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}piperazine

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Ethoxyacetic acid	HCID 12301	—
Reactant	Tetrafluoro-m-phenylenediamine dihydrochloride	HCID 149026	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone	HCID 11427553	—
Product	(E)-4-ethoxyacetyl-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}piperazine	HCID 67089618	20%

Reaction Steps

The crude product obtained using dihydrochloride of Compound 18 (300 mg, 0.741 mmol), N-methylmorpholine (0.163 mL, 1.48 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (199 mg, 1.04 mmol), 1-hydroxybenzotriazole monohydrate (130 mg, 0.963 mmol) and ethoxyacetic acid (0.0700 mL, 0.741 mmol) in a similar manner to Example 5, was purified by silica gel column chromatography (chloroform/methanol=90/10), followed by recrystallization from mixed solvent of ethyl acetate/methanol to obtain Compound 128 (62.0 mg, 20%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07470717B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-80b137bbfa514ed1ae1758c79df77cdb
Source note	uspto-grants-2008_12