Trifluoroacetic acid → 3-(3-(cyclopropanecarboxamido)-1H-indazol-6-ylamino)-4-methyl-N-(3-(trifluoro-methyl)phenyl)benzamide

To a solution of 3-(3-(cyclopropanecarboxamido)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-ylamino)-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide (25 mg) in CH2Cl2 (1 mL) was added TFA (0.25 mL) at room temperature. The reaction mixture was stirred for 2 hours and the organic solvent was concentrated under reduced pressure. To a solution of the resulting mixture in THF (0.5 mL) and MeOH (0.5 mL) was added LiOH aqueous solution (1.0 M, 1.0 mL). The resulting mixture was stirred for another 2 hours at room temperature. The organic solvent was removed under reduced pressure and the aqueous layer was extracted with ethyl acetate. The organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by Prep HPLC and acetonitrile was removed under reduced pressure. The remained water was freeze-dried to afford TFA salt of title compound (16 mg, 66%), MS (ESI) m/z 494 (M+H)+.

1. concentrationthe organic solvent was concentrated under reduced pressure
2. additionTo a solution of the resulting mixture in THF (0.5 mL) and MeOH (0.5 mL) was added LiOH aqueous solution (1.0 M, 1.0 mL)
3. stirringThe resulting mixture was stirred for another 2 hours at room temperature
4. customThe organic solvent was removed under reduced pressure
5. extractionthe aqueous layer was extracted with ethyl acetate
6. washThe organic extracts were washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by Prep HPLC and acetonitrile
10. customwas removed under reduced pressure
11. dry with materialThe remained water was freeze-dried

ORD-Eintrag

ord-9baaf77a3f124a35afddd07456819914

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08987275B2