p-Anisoyl chloride → N-(4-chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-methoxybenzamide

Participants

Role	Name	HCID	Charge
Reactant	p-Anisoyl chloride	HCID 7477	—
Reactant	Piperidine	HCID 8082	—
Reactant	2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine	HCID 3513851	—
Reactant	HCID 66691716	HCID 66691716	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	1,2-Dichloroethane	HCID 11	—
Product	N-(4-chloro-5-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)-2-nitrophenyl)-4-methoxybenzamide	HCID 66693771	74.9%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of (4-(5-amino-2-chloro-4-nitrophenyl)piperazin-1-yl)(3-(2-methoxyphenyl)-5-methylisoxazol-4-yl)methanone (16 mg, 0.034 mmol, Preparation L), 4-methoxybenzoyl chloride (12 mg, 0.068 mmol), DMAP (6 mg, 0.034 mmol), and BEMP (19 mg, 0.068 mmol) in DCE (1 mL) was heated at 80° C. for 3 h. Cooled down to RT, the mixture was treated with piperidine (0.3 ml) for 1 h and concentrated in vacuo. HPLC purification gave the title compound (15.7 mg, 0.025 mmol, 74.9% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08362004B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-ae02d8f5d23f492d888d36442dc9081c
Source note	uspto-grants-2013_01