Diisopropylethylamine → 4-[4-(4-tert-butyl-phenyl)-piperazin-1-yl]-1-[(R)-3-(4-nitro-3-trifluoromethyl-phenylamino)-pyrrolidin-1-yl]-butan-1-one

To as suspension of 4-[4-(4-tert-butylphenyl)-piperazin-1-yl]-butyric acid lithium salt (15 mg; 0.05 mmol, prepared in accord with Example 167) in tetrahydrofuran (1 mL) is added a solution of tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) in dimethylformamide (0.5 mL). After 15 minutes at room temperature, diisopropylethyl amine (25 μL; 0.15 mmol) and a solution of (4-nitro-3-trifluoromethyl-phenyl)-(R)-pyrrolidin-3-yl-amine hydrochloride (16 mg; 0.05 mmol, prepared in accord with Example 165) in dimethylformamide (0.5 mL) is added and the reaction mixture is stirred at room temperature for one hour. Aluminium oxide (90 active basic) is then added and stiffing is continued. The solids are removed by filtration and the filtrate is concentrated under high vacuum. The obtained residue is purified by preparative HPLC to afford the desired compound (17 mg; 0.030 mmol). The structure was confirmed using Protocol I-D. Calculated mass=562; observed mass=562; HPLC retention time=1.60 min.

1. customThe solids are removed by filtration
2. concentrationthe filtrate is concentrated under high vacuum
3. customThe obtained residue is purified by preparative HPLC

ORDレコード

ord-b179ae3cbdc8478c9d04ab9f279c6148

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09096524B2