1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Benzamide

DIPEA (397 mg, 3.08 mmol) was added drop wise to 4-(hydroxybenzoyl amino)-acetic acid (200 mg, 1.03 mmol) in DMF (6 mL). EDCI (294 mg, 1.54 mmol) and HOBT (166 mg, 1.23 mmol) were added consecutively and, after 15 mins, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone (390 mg, 1.33 mmoles) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 70:30 EtOAc:hexane as eluent) afforded 4-hydroxy-N-[2-Oxo-2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl]-benzamide in 65% yield. LC-MS purity: 93%, 1H NMR (DMSO-D6): δ 10 (s, 1H), 8.3 (d, 1H), 7.8 (m, 5H), 7.5 (t, 1H), 6.8 (d, 2H), 4.1 (d, 2H), 3.6 (m, 5H), 3.1 (m, 3H).

1. extractionthe product was extracted with EtOAc
2. washThe organic layer was washed with brine
3. dry with materialdried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customto afford the crude product
6. customPurification

ORD 기록

ord-d30d8be59e8e41019e5360151f220cdc

출처 데이터셋

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07842696B2