Water → N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	5-Bromo-2-fluorobenzoic acid	HCID 2736315	—
Reactant	4-Methoxybenzene-1,2-diamine dihydrochloride	HCID 3085161	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamide	HCID 63257662	62.4%

Reaction Steps

Method 6—Step a A mixture of 5-Bromo-2-fluoro-benzoic acid (1.50 g, 6.85 mmol), 4-methoxy-benzene-1,2-diamine dihydrochloride (1.77 g, 8.49 mmol), HATU (2.73 g, 7.19 mmol) and TEA (2.88 mL, 20.76 mmol) in dichloromethane (20 mL) and DMF (5 mL) was stirred at room temperature overnight, then water was added (50 mL), mixture was stirred for 2 h and left standing at room temperature overnight. The precipitate obtained was filtered off and dried to afford 1.45 g of the title compound (50%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08835648B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-d73d945322a94c8a9a3b8a50b768d317
Source note	uspto-grants-2014_09