Diisopropylethylamine → Ethyl 4-(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-4-oxobutanoate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Ethoxy-4-oxobutanoate	HCID 1711967	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	Hydrogen chloride-ethyl acetate	HCID 21866389	—
Reactant	HCID 67548869	HCID 67548869	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Product	Ethyl 4-(7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-4-oxobutanoate	HCID 67549783	38.3%

Reaction Steps

The same operation as in Example (93a) was performed using tert-butyl 7-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate obtained in Example (95c) (0.11 g, 0.27 mmol), a 4 N hydrochloric acid/ethyl acetate solution (8 ml, 32 mmol), monoethyl succinate (150 mg, 1 mmol), WSC hydrochloride (288 mg, 1.5 mmol), N,N-diisopropylethylamine (0.52 g, 4 mmol) and DMAP (10 mg). Purification by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1, 2/1, 2/3, 0/1) gave 45 mg of the title compound as a light yellow solid (38%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08536197B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-b329bccfa4f845fe82922597a6f5b049
Source note	uspto-grants-2013_09