Acetic Acid → HCID 71523527、化合物

温度

2.5 °C

To a cooled mixture (0-5° C.) of 3-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)propanoic acid (40 mg, 0.11 mmol) in CH2Cl2 (1 mL), 1′1′-carbonyldiimidazole (CDI) (17.4 mg, 0.11 mmol) was added. After the mixture was stirred for 2 h at 0-5° C., methansulfonamide (10 mg, 0.11 mmol) and diazobicyclo-[5.4.0]undec-7-ene (DBU) (16.1 μL, 0.11 mmol) were added. The mixture was left stirring overnight. Glacial AcOH (13.2 μL) was added, the reaction mixture was diluted with CH2Cl2 (1 mL), and the organic layer was washed with 10% NaH2PO4 (pH 4) (1×1 mL) and water (3 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a crude residue that was purified by flash chromatography (SiO2, ethyl acetate/hexane, 0.5% AcOH gradient) to afford the title compound as a bright yellow solid (32 mg, 66%). C21H21ClN2O5S, Mr=448.92; 1H NMR (400 MHz, DMSO-d6) d: 2.21 (s, 3H), 2.55 (t, J=7.2 Hz, 2H), 3.11 (t, J=7.2 Hz, 2H), 3.16 (s, 3H), 3.75 (s, 3H), 6.43 (d, J=9.2 Hz, 1H), 6.64 (dd, J=9.0 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H), 7.64-7.69 (m, 4H); LCMS (ESI) tR: 2.74 min (>95%, UV254, ELSD), m/z: 249.1 [M+1]+.

1. waitThe mixture was left
2. stirringstirring overnight
3. washthe organic layer was washed with 10% NaH2PO4 (pH 4) (1×1 mL) and water (3 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give a crude residue that
8. customwas purified by flash chromatography (SiO2, ethyl acetate/hexane, 0.5% AcOH gradient)

ORDレコード

ord-3560f5db3cc445d89570358698f2c5ec

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09346803B2