Diisopropylethylamine → {4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2'-methylbiphenyl-2-YL}methanol

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2-(Hydroxymethyl)-2'-methylbiphenyl-4-carboxylic acid	HCID 59495734	—
Reactant	5-fluoro-N'-hydroxy-2-methoxybenzenecarboximidamide	HCID 72336823	—
Solvent	Acetonitrile	HCID 6342	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2'-methylbiphenyl-2-YL}methanol	HCID 25255481	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

Intermediate 23 (276 mg; 1.5 mmol; 1 eq.), Intermediate 41 (436 mg; 1.8 mmol; 1.2 eq.) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (345 mg; 1.8 mmol; 1.2 eq.) were dissolved in THF (6 mL) and acetonitrile (6 mL) and the reaction mixture was stirred at room temperature for 2 hours. DIEA (0.61 mL; 3.6 mmol; 2.4 eq.) was added and the mixture was heated in the microwave at 150° C. for 30 min. The reaction mixture was then filtered through a SPE-NH2 column (2 g) and through a SPE-SCX column (2 g) and rinsed with ACN. The filtrate was evaporated and the residue washed with ACN to afford the title compound as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889668B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-fee5f96c193a4464ac5a4ced30751e8c
Source note	uspto-grants-2014_11