Diisopropylethylamine → 1-[4-(4-Nitro-3-trifluoromethyl-phenylamino)-piperidin-1-yl]-3-[4-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-piperazin-1-yl]-propan-1-one

3-[4-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-propionic acid lithium salt (15 mg; 0.05 mmol, prepared in accordance with Example 123) and tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) are diluted in a 2 to 1 mixture of dimethylformamide and tetrahydrofuran (0.75 mL). A solution of (4-nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride (16 mg; 0.05 mmol, prepared in accordance with Example 8) in dimethylformamide (0.25 mL) and diisopropylethyl amine (25 μL; 0.15 mmol) are added and the reaction is then stirred. After 4 hours at room temperature, aluminium oxide (90 active basic) is added and stirring is continued for 40 minutes. 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 (16 mg; 0.027 mmol). The structure was confirmed using Protocol I-D. Calculated mass=582; observed mass=582; HPLC retention time=1.41 min.

1. stirringstirring
2. waitis continued for 40 minutes
3. customThe solids are removed by filtration
4. concentrationthe filtrate is concentrated under high vacuum
5. customThe obtained residue is purified by preparative HPLC

ORD 기록

ord-cd263e21622541098ef41e4c1dae4ab3

출처 데이터셋

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09096524B2