3-(Trifluoromethoxy)benzoic acid → N-(3-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-methylphenyl)-3-(trifluoromethoxy)benzamide

A solution of N-{5-[(5-amino-2-methylphenyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamide (120 mg, 382 μmol) produced in Example D35(v), 3-(trifluoromethoxy)benzoic acid (102 mg, 500 μmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (189 mg, 500 μmol) in pyridine (4 mL) was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (15 mL), and the mixture was extracted with ethyl acetate (20 mL, 5 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→95/5), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from tetrahydrofuran to give the title compound (78 mg, 40%) as colorless crystals.

1. extractionthe mixture was extracted with ethyl acetate (20 mL, 5 mL)
2. washThe combined organic layer was washed with saturated brine (5 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationThe insoluble material was filtered off
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→95/5)
7. additionthe fractions containing the object product
8. concentrationwere concentrated under reduced pressure
9. customThe obtained residue was recrystallized from tetrahydrofuran

ORDレコード

ord-245720cb7bf54dc78c3ff02b5564c45c

出典データセット

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08344135B2