Diisopropylethylamine → N-(2-t-Butoxycarbonylaminophenyl)-6-hydroxymethylpyridine-3-carboxylic acid amide

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylethylamine	HCID 81531	—
反応物	N-(tert-Butoxycarbonyl)-1,2-phenylenediamine	HCID 676311	—
反応物	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
反応物	6-(Hydroxymethyl)pyridine-3-carboxylic acid	HCID 14722130	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	N-(2-t-Butoxycarbonylaminophenyl)-6-hydroxymethylpyridine-3-carboxylic acid amide	HCID 59225157	67%

反応手順

2-Aminophenyl carbamic acid t-butyl ester (Reference Compound No. 1-1, 0.60 g, 2.9 mmol), N,N-diisopropylethylamine (1.5 mL, 8.6 mmol), and HATU (1.1 g, 2.9 mmol) were added to a suspension of 6-hydroxymethylpyridine-3-carboxylic acid (Reference Compound No. 10-1) in DMF (10 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Water (200 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL, 50 mL), and then the organic layer was washed with brine (100 mL) twice. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 0.66 g of the title reference compound as a brown oil. (Yield 67% in 2 steps)

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08012972B2
出典データセット	uspto-grants-2011_09
ORD ID	ord-507c104362d54aae8ff4f70b63a6d2b5
出典メモ	uspto-grants-2011_09