Details

Autor(en) / Beteiligte

• Reddy, Srinivasa E

Titel

I. A scalable synthesis of N-[4-chloro-3-(trifluoromethyl) phenyl]-({4-[2-(N-methyl-carbamoyl) (4-pyridyloxy)] phenyl} amino) carboxamide. II. A scalable synthesis of 4-bromo-6-methoxy quinoline. III. Synthesis of 3'-O-methylguanosine

Ort / Verlag

ProQuest Dissertations & Theses

Erscheinungsjahr

2005

Link zum Volltext

• ProQuest

Quelle

ProQuest Dissertations & Theses A&I

Beschreibungen/Notizen

• I. It was reported1 that the overall yield of N-[4-chloro-3-(trifluoromethyl) phenyl]-({4-[2-(N-methyl-carbamoyl)(4pyridyloxy)]phenyl}amino)carboxamide 1,a potent raf kinase inhibitor was 63%. The overall yield was increased to greater than 90% by manipulating reaction conditions and certain reagents in the synthetic scheme. II. 4-Bromo-6-methoxyquinoiine was synthesized 2, 3 in quantitative yield in 3 steps. The second step in the synthesis involved the use of Dowtherm A, a high boiling liquid, as a heat transfer solvent. The final product contained Dowtherm A as an impurity in a 1:1 ratio leading to an inefficient and impure synthesis of 4-bromo-6-methoxy quinoline. A way was found to make the synthesis more efficient and to make a pure final compound by replacing Dowtherm A with an alternative solvent and by developing a technique to remove Dowtherm A impurities from the final product. III. 3'-O-Methylguanosine was synthesized in two steps. We did process development investigations on both these steps to attain the higher purity and a quantitative yield of the product.