1,2-Cyclopropanedicarboxylic acid, trans- → trans-2-(4-(2,6-Dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid

온도

70 °C

To a solution of N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (141 mg, 0.50 mmol), trans-cyclopropane-1,2-dicarboxylic acid (325 mg, 2.5 mmol), and disiopropylethylamine (339 mg, 2.63 mmol) in dry DMF (5 mL) was added HATU (1951 mg, 2.5 mmol). The reaction mixture was heated at 70° C. for 6 hours and then quenched with sat. NH4Cl (100 mL). The mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by prep HPLC (10-50% CH3CN/H2O with 0.1% formic acid) to give trans-2-(4-(2,6-dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid (132 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6) δ 11.14 (s, 1H), 10.86 (s, 1H), 8.38 (s, 1H), 8.23 (d, J=5.6 Hz, 1H), 7.62-7.55 (m, 2H), 7.54-7.45 (m, 2H), 1.90-1.82 (m, 1H), 1.25 (dt, J=8.0, 5.4 Hz, 3H). LCMS (ESI) m/z: 394.0 [M+H+].

1. customquenched with sat. NH4Cl (100 mL)
2. extractionThe mixture was extracted with EtOAc (3×100 mL)
3. dry with materialThe combined organic extracts were dried with Na2SO4
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by prep HPLC (10-50% CH3CN/H2O with 0.1% formic acid)

ORD 기록

ord-13fb0baad3b6493383d1043c18e0046a

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08486950B2