2,3-Diaminobenzoic acid → (S)-2-(2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

https://huagongshe.com/ja/reaction/85134

関与物質

役割	名称	HCID	仕込み量
反応物	2,3-Diaminobenzoic acid	HCID 198069	—
反応物	Sodium Pyrosulfite	HCID 656671	—
反応物	HCID 86653795	HCID 86653795	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	(S)-2-(2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid	HCID 67202420	51%

反応条件

温度	110 °C

反応手順

To a solution of (S)-2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde (66; 1.83 g, 6.40 mmol) in DMF (150 ml) was added 2,3-diaminobenzoic acid (1; 0.97 g, 6.40 mmol), and Na2S2O5 (1.82 g, 9.60 mmol). The reaction mixture was stirred at 110° C. for 18 h. It was then cooled to room temperature and diluted with water. The resulting solids were collected by filtration and dried to afford (S)-2-(2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 67 as dark yellow solid (0.84 g, 51%). MS (ESI) calcd for C21H20F2N5O5: 418.13; found: 419 [M+H].

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08846947B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-6429a796ca9840f98860e61305a0406f
出典メモ	uspto-grants-2014_09