3-Pyridinemethanol → 4-(3-Bromo-4-fluorophenyl)-3-{4-[(pyridin-3-ylmethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one trifluoroacetate

関与物質

役割	名称	HCID	仕込み量
反応物	3-Pyridinemethanol	HCID 7510	—
反応物	Triphenylphosphine	HCID 11776	—
反応物	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
反応物	N-[4-[4-(3-Bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl]-2,2,2-trifluoroacetamide	HCID 58755133	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	4-(3-Bromo-4-fluorophenyl)-3-{4-[(pyridin-3-ylmethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one trifluoroacetate	HCID 67435030	6.6%

反応条件

温度	25 °C

反応手順

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-2,2,2-trifluoroacetamide (50 mg, 0.11 mmol), nicotinyl alcohol (14 μL, 0.15 mmol), and triphenylphosphine (42 mg, 0.16 mmol) in tetrahydrofuran (0.35 mL) at 0° C. was treated with diisopropyl azodicarboxylate (34 μL, 0.17 mmol). The reaction mixture was stirred at 25° C. for 16 h and purified by preparative LCMS to give the desired product (4 mg, 6%). LCMS for C16H11BrFN6O3 (M+H)+: m/z=432.9, 434.9.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08034953B2
出典データセット	uspto-grants-2011_10
ORD ID	ord-33b53191e04a4bc6900732f2fa32c34d
出典メモ	uspto-grants-2011_10