4-Fluorobenzoic Acid → 4-Fluoro-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]benzamide

関与物質

役割	名称	HCID	仕込み量
反応物	4-Fluorobenzoic Acid	HCID 9973	—
反応物	Sodium Bicarbonate	HCID 516892	—
反応物	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
反応物	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
反応物	2-Amino-4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazole	HCID 86612468	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	4-Fluoro-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]benzamide	HCID 23144791	23%

反応条件

温度	80 °C

反応手順

Compound 454 (834 mg, 3.00 mmol) was dissolved in DMF (12 mL), and 4-fluorobenzoic acid (3.36 g, 24.0 mmol), EDC hydrochloride (4.12 g, 24.0 mmol) and 1-hydroxybenzotriazole monohydrate (3.68 g, 24.0 mmol) were added thereto, followed by stirring at 80° C. for 2 hours. The reaction mixture was poured into a mixture of a saturated aqueous solution of sodium hydrogencarbonate (30 mL) and water (30 mL), and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (chloroform:methanol=19:1), followed by recrystallizing from ethanol to afford the entitled Compound 468 (270 mg, 23%) as a white solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08889718B2
出典データセット	uspto-grants-2014_11
ORD ID	ord-fea6a924c9f64d19854f112c812b5662
出典メモ	uspto-grants-2014_11