Triethylamine → N-[4-(3-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-(3-pyridyl)acetamide

https://huagongshe.com/en/reaction/337521

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	3-Pyridineacetic acid, hydrochloride (1:1)	HCID 2723724	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	2-Amino-4-(3-furyl)thiazol-5-yl tetrahydropyran-4-yl ketone	HCID 86612473	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-[4-(3-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-(3-pyridyl)acetamide	HCID 23144488	52%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Compound 610 (102 mg, 0.366 mmol) was dissolved in DMF (3 mL), and 3-pyridylacetic acid hydrochloride (635 mg, 3.66 mmol), EDC hydrochloride (702 mg, 3.66 mmol), 1-hydroxybenzotriazole monohydrate (561 mg, 3.66 mmol) and triethylamine (0.510 mL, 3.66 mmol) were added thereto, followed by stirring at 80° C. for 10 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (hexane:ethyl acetate=2:1), followed by recrystallizing from a mixed solvent of ethanol and water to afford the entitled Compound 618 (74.6 mg, 52%) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889718B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-3409140231b94442b0a15d302f1eaa29
Source note	uspto-grants-2014_11