2,4-Dichloro-5-methoxyaniline → 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile

Participants

Role	Name	HCID	Charge
Reactant	2,4-Dichloro-5-methoxyaniline	HCID 1476636	—
Reactant	Pyridinium chloride	HCID 10176127	—
Reactant	4-Chloro-7-fluoro-6-[2-(4-morpholinyl)ethoxy]-3-quinolinecarbonitrile	HCID 23498093	—
Product	4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile	HCID 23498101	—

Reaction Steps

Following the procedure of Reference Example 8, a mixture of 4-chloro-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile (136 mg, 0.41 mmol), 2,4-dichloro-5-methoxyaniline (90.5 mg, 0.47 mmol) and pyridine hydrochloride (95 mg, 0.82 mmol) provides, after preparative thin layer chromatography eluting with 7% methanol in dichloromethane, 58 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile, mp 166-168° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06780996B2
Source dataset	uspto-grants-2004_08
ORD ID	ord-2a564c0ef419407a99b1c7c60c18d3de
Source note	uspto-grants-2004_08