2-Naphthylalanine → Methyl-(1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	2-Naphthylalanine	HCID 185915	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	1-(2-Chloroethyl)-3-(2-methylquinolin-4-yl)urea	HCID 2344366	—
Reactant	3-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine	HCID 2761404	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Methyl-(1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester	HCID 59715909	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

A mixture of methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (10 mmol), 1-(2-chloro-ethyl)-3-(2-methyl-quinolin-4-yl)-urea (10 mmol), NaHCO3 (20 mmol), Nal (0.5 mmol), and THF (70 mL) is stirred in a sealed vessel at 70° C. for 6 d. The reaction mixture is filtered, evaporated to dryness, and the residue is purified by preparative HPLC to provide the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07375227B2
Source dataset	uspto-grants-2008_05
ORD ID	ord-0c2153306fe145dd8438a4cfac13ed62
Source note	uspto-grants-2008_05