1-Hydroxybenzotriazole → HCID 58778945, compound

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	Methyl 2-(4-amino-3-chlorophenyl)acetate	HCID 13616273	—
Reactant	HCID 17859248	HCID 17859248	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 58778945	HCID 58778945	51.2%

Reaction Steps

In DMF (5 ml) were dissolved 7-fluoro-1-isoquinolinecarboxylic acid (250 mg, 1.31 mmol), methyl 4-amino-3-chlorophenylacetate (262 mg, 1.31 mmol), HOBt (catalytic amount), and DMAP (192 m g, 1.57 mmol). To the resulting solution was added EDC HCl (290 mg, 6.93 mmol), followed by stirring at room temperature for 14 hours. The reaction mixture was poured into water (20 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with ether and then dried under reduced pressure to give methyl (3-chloro-4-((7-fluoro-1-isoquinolinylcarbonyl)amino)phenyl)acetate (250 mg, 51%) as a colorless crystalline powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07157487B2
Source dataset	uspto-grants-2007_01
ORD ID	ord-9223936bfeca43749140ddc818aefe5f
Source note	uspto-grants-2007_01