1,2-Dichloroethane → N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-3-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-5-carboxamide

温度

0 °C

To a stirred solution of 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine (bis TFA salt, 108 mg, 0.26 mmol) in DCM (3 mL) at 0° C. was added trimethyl aluminium (2 M in toluene, 0.13 mL, 0.26 mmol) and the mixture was stirred at 0° C. for 15 min. Ethyl 3-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-5-carboxylate (50 mg, 0.13 mmol) was added dropwise as a solution in DCM (2 mL), followed by TEA (0.045 mL, 0.32 mmol). The reaction was stirred at ambient temperature for 18 h, after which time TEA (0.110 mL, 0.79 mmol) and DCE (4 mL) were added. The reaction was heated to 60° C. for 18 h, then partitioned between saturated aqueous NH4Cl (20 mL) and EtOAc (2×20 mL). The aqueous layer was extracted with DCM (2×10 mL) and these extracts were dried over MgSO4 and solvents were removed in vacuo. A portion of the product was purified using prep method A.

1. stirringThe reaction was stirred at ambient temperature for 18 h
2. temperatureThe reaction was heated to 60° C. for 18 h
3. custompartitioned between saturated aqueous NH4Cl (20 mL) and EtOAc (2×20 mL)
4. extractionThe aqueous layer was extracted with DCM (2×10 mL)
5. dry with materialthese extracts were dried over MgSO4 and solvents
6. customwere removed in vacuo
7. customA portion of the product was purified

ORDレコード

ord-ecef3fe7f1ae43e69334b9de18d218a1

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08623859B2