Triethylamine → N-Benzyloxy-4-chloro-2-cyclopropylamino-5-fluoro-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,1'-Carbonyldiimidazole	HCID 68263	—
Reactant	Benzyloxyamine hydrochloride	HCID 102312	—
Reactant	4-Chloro-2-cyclopropylamino-5-fluoro-benzoic acid	HCID 22632883	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-Benzyloxy-4-chloro-2-cyclopropylamino-5-fluoro-benzamide	HCID 22632989	100.3%

Reaction Steps

Following the procedure of Example A, 4-chloro-2-cyclopropylamino-5-fluoro-benzoic acid (Example C-3, 2.0 g, 8.7 mmol) was reacted with carbonyldiimidazole (1.7 g, 10.5 mmol), O-benzylhydroxylamine hydrochloride (1.67 g, 10.5 mmol), and triethylamine (1.5 mL, 10.5 mmol) in THF (50 mL) to give 2.92 g of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06825199B2
Source dataset	uspto-grants-2004_11
ORD ID	ord-cfaf755792694a3fa66e5635098d94cb
Source note	uspto-grants-2004_11