Dimethylamine → N-[2-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-yl]-5-(N,N-dimethylcarbamoyl)-nicotinamide

A suspension of pyridine-3,5-dicarboxylic acid (43.5 mg, 0.26 mmol) in 2.5 mL of SOCl2 was refluxed for 2.5 h to give a light yellow solution. The excess SOCl2 was removed by distillation and the resulting solid was dissolved in 2 mL of dry THF. Triethylamine (0.12 mL, 0.86 mmol) and a solution of 7-aminobenzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (39 mg, 0.087 mmol) in 2 mL of THF was added and the reaction mixture was stirred 12 h. A solution of dimethylamine (2.0 M in THF, 1 mL, 2 mmol) was added and the reaction mixture was stirred for additional 5 h. The reaction mixture was then extracted with EtOAc and purified by reverse phase HPLC on a C18 column eluting with an acetonitrile-water gradient to provide 12 mg (24%) of the title compound.

1. temperaturewas refluxed for 2.5 h
2. customto give a light yellow solution
3. customThe excess SOCl2 was removed by distillation
4. dissolutionthe resulting solid was dissolved in 2 mL of dry THF
5. stirringthe reaction mixture was stirred for additional 5 h
6. extractionThe reaction mixture was then extracted with EtOAc
7. custompurified by reverse phase HPLC on a C18 column
8. washeluting with an acetonitrile-water gradient

ORDレコード

ord-ab0dcebdf9f04b88ac7f3359e683c096

出典データセット

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07550461B2