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HRID 658194作成日:2026年10月27日

Dimethylformamide → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

https://huagongshe.com/reaction/658194

反応式

関与物質

役割名称HCID仕込み量
反応物DimethylformamideHCID 6228—
反応物DiisopropylethylamineHCID 81531—
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(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 12494972—
反応物6-Nitro-1-benzofuran-2-carboxylic acidHCID 13190726—
生成物N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamideHCID 59341430—

反応手順

1040 mg (5.02 mmol) of 6-nitrobenzofuran-2-carboxylic acid, 1000 mg (5.02 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 2290 mg (6.03 mmol) of HATU, 2250 mg (18.08 mmol) of N,N-diisopropylethylamine and 9 ml of DMF are reacted according to the general procedure (variant B). DMF is removed under reduced pressure. The product is taken up in 100 ml of 1N aqueous sodium hydroxide solution and extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are washed eight times with 1N aqueous sodium hydroxide solution and once with saturated sodium chloride solution and then dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. 1.34 g (79% of theory) of the title compound are obtained.

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US08076355B2
出典データセットuspto-grants-2011_12
ORD IDord-f759dba97f0241ec83103bde539445d7
出典メモuspto-grants-2011_12