1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-N-(2-methoxy-5-nitrophenyl)-acetamide

Participants

Role	Name	HCID	Charge
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	5-Methoxy-2-nitroaniline	HCID 85300	—
Reactant	Propan-2-one--dichloromethane (1/1)	HCID 21584124	—
Reactant	HCID 22054464	HCID 22054464	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-N-(2-methoxy-5-nitrophenyl)-acetamide	HCID 22054461	12%

Reaction Steps

[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-acetic acid (0.075 g, 0.2 mmol), EDCI (0.055 g, 0.3 mmol), 2-Nitro-5-methoxyaniline (0.044 g, 0.26 mmol), DMAP (0.005 g, 0.04 mmol) in dichloromethane (4.5 ml) and DMF (0.75 ml) react for 5 h in a fashion similar to that of Example 3. Column chromatography (silica gel, acetone/dichloromethane gradient) gives the title compound (0.012 g, 12%). Mass Spectrum (FIA) (m/z) 520.2 [M+1]

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07064131B2
Source dataset	uspto-grants-2006_06
ORD ID	ord-a73b5c71d0b34e8dbb25ffc9ff8b340a
Source note	uspto-grants-2006_06