Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzofuran-2-carboxamide

3.8 g (15.77 mmol) of 6-bromobenzofuran-2-carboxylic acid (Example 1A), 3.14 g (15.77 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 7.19 g (18.92 mmol) of HATU, 7.34 g (56.76 mmol) of N,N-diisopropylethylamine and 50 ml of DMF are reacted by general method C. The crude product is taken up in methanol and shaken together with acidic ion exchanger (Dowex® WX2-200) for about 20 min. The loaded ion exchanger is washed successively with methanol, dichloromethane and again with methanol. The product is eluted with methanol/triethylamine 90:10. The solvent is removed in a rotary evaporator under reduced pressure. Finally, the last residues of solvent are removed under high vacuum. 5.14 g (85% of theory) of the title compound are isolated. For analysis, a small amount is converted into the hydrochloride with 4 N hydrogen chloride in dioxane.

1. washThe loaded ion exchanger is washed successively with methanol, dichloromethane and again with methanol
2. washThe product is eluted with methanol/triethylamine 90:10
3. customThe solvent is removed in a rotary evaporator under reduced pressure
4. customFinally, the last residues of solvent are removed under high vacuum

ORDレコード

ord-ca97488e0c5b48c48236783b99b4c72e

出典データセット

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07977485B2