2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]amide → HCID 71288910、化合物

温度

80 °C

To a solution of 1-methyl-3-tributylstannanyl-1H-thieno[3,2-c]pyrazole (111 mg, 0.26 mmol) and 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide (120 mg, 0.24 mmol) in DMF (1.2 mL) were added Pd(PPh3)4 (14 mg, 0.012 mmol) and copper(I) iodide (9 mg, 0.05 mmol). The yellow reaction mixture was purged with argon then heated at 80° C. for 1.5 h then cooled to room temperature, quenched with sat NH4Cl and extracted with EtOAc (2×). The combined organics were washed with sat LiCl and brine then dried over MgSO4 and concentrated. The crude residue was purified by silica gel chromatography with 50% to 100% EtOAc/heptane to provide 131 mg (98%) of 2-(1-methyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide as an off-white solid.

1. customThe yellow reaction mixture was purged with argon
2. temperaturethen cooled to room temperature
3. customquenched with sat NH4Cl
4. extractionextracted with EtOAc (2×)
5. washThe combined organics were washed with sat LiCl and brine
6. dry with materialthen dried over MgSO4
7. concentrationconcentrated
8. customThe crude residue was purified by silica gel chromatography with 50% to 100% EtOAc/heptane

ORDレコード

ord-b1c1f5fdbf0b42b4abaf583a5cfc243f

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08658646B2