1-Hydroxybenzotriazole → 4-benzyloxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

関与物質

役割	名称	HCID	仕込み量
反応物	1-Hydroxybenzotriazole	HCID 75771	—
反応物	Diisopropylethylamine	HCID 81531	—
反応物	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
反応物	1-(2-Trifluoromethylbenzoyl)piperazine hydrochloride	HCID 16733783	—
反応物	{[4-(Benzyloxy)phenyl]formamido}acetic acid	HCID 23931762	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	4-benzyloxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide	HCID 57855661	104.1%

反応手順

DIPEA (98 mg, 0.76 mmol) was added to a stirred solution of (4-benzyloxy-benzoylamino]-acetic acid (50 mg, 0.17 mmol) in DMF (3 mL). HOBT (25.8 mg, 0.19 mmol) and EDCI.HCl (83 mg, 0.43 mmol) were added at room temperature. After 2 minutes, piperazine-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (61.5 mg, 0.21 mmol). The resulting mixture was stirred at room temperature overnight. The mixture was diluted with cold water and the resulting precipitate was filtered, washed with hexane and dried to afford 93 mg (99% yield) of 4-benzyloxy-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LC-MS purity: 87%, 1H NMR (DMSO): δ 8.5 (s, 1H,), 7.8 (m, 5H), 7.5 (s, 1H), 7.4 (m, 4H), 7.1 (d, 2H), 5.2 (s, 2H), 4.2 (d, 2H), 3.7 (m, 4H), 3.5 (s, 2H), 3.4 (s, 2H), 3.3 (s, 2H).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07842696B2
出典データセット	uspto-grants-2010_11
ORD ID	ord-6302d29bbce141e88cc21d9c1039d7ef
出典メモ	uspto-grants-2010_11