4-(2-Propyn-1-yl)morpholine → {4-[3-(2-Cyclohexyl-ethoxy)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid Ethyl Ester

Participants

Role	Name	HCID	Charge
Reactant	4-(2-Propyn-1-yl)morpholine	HCID 412941	—
Reactant	[4-(3-Bromo-5-cyclopentylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester	HCID 57791902	—
Reactant	{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester	HCID 67024299	—
Product	{4-[3-(2-Cyclohexyl-ethoxy)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic Acid Ethyl Ester	HCID 67171335	—

Reaction Steps

The title product was prepared from {4-[3-Bromo-5-cyclopentylmethoxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (260 mg; 0.54 mmol) and 4-prop-2-ynyl-morpholine (203.6 mg; 1.63 mmol) applying the procedure described for {4-[3-[2-(4-Chlorophenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester. The crude product was purified by preparative HPLC (method B). Yield: 80 mg (28%). HPLC-MS: m/z: 523.9 (M)+; Rt: 2.19 min

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07943669B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-c8038208d75d479f93484821674a77e8
Source note	uspto-grants-2011_05