Methanol → 2-[[(1,6-Dihydro-6-oxo-3-pyridinyl)methyl]amino]-N-[4-propynyl-3-(trifluoromethyl)phenyl]benzamide

A mixture of 2-[[6-methoxy-3-pyridinyl]methyl]amino-N-[4-(1-propynyl)-3-(trifluoromethyl)-phenyl]benzamide (step 4.1; 1.10 g, 2.5 mmol) and trimethylsilyl iodide (Fluka, Buchs, Switzerland; 1.0 mL, 7.5 mmol) in chloroform (30 mL) is stirred at 60° C. for 16 hours under an argon atmosphere. The cooled mixture is then treated with methanol (2 mL) and stirred at room temperature for 10 minutes. The solvent is evaporated under reduced pressure and the residue is treated with an aqueous solution of ammonia (100 mL of 5%) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with saturated aqueous sodium chloride (50 mL), dried (MgSO4), filtered and the solvent is evaporated under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent ethyl acetate and recrystallised from hot ethyl acetate hexane to give the title compound as a colourless crystalline solid; m.p. 208–212° C.

1. stirringstirred at room temperature for 10 minutes
2. customThe solvent is evaporated under reduced pressure
3. additionthe residue is treated with an aqueous solution of ammonia (100 mL of 5%)
4. extractionextracted with ethyl acetate (3×100 mL)
5. washThe combined extracts are washed with saturated aqueous sodium chloride (50 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customthe solvent is evaporated under reduced pressure
9. customto yield the crude product which
10. customis purified by column chromatography on silica gel, eluent ethyl acetate
11. customrecrystallised from hot ethyl acetate hexane

ORDレコード

ord-4df73740e5ab472bbaeaa1adeac83fca

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091224B2