Triethylamine → HCID 46215557、化合物

To a 100 mL round bottomed flask was added 2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)nicotinic acid (0.3031 g, 0.834 mmol), cyclopropylmethanamine (0.0869 g, 1.22 mmol), and triethylamine (0.347 mL, 2.50 mmol) in N,N-dimethylformamide (3 mL) to stir for 5 min. HATU (0.3955 g, 0.917 mmol) was then added and allowed to stir overnight. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extract was washed with water (1×10 mL), saturated sodium chloride (1×10 mL), saturated sodium bicarbonate (1×10 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini™ column, 5 micron, 150×30 mm, 0.1% trifluoroacetic acid in acetonitrile/water, gradient 10% to 100% over 15 min. The product was taken up in DCM and extracted with saturated sodium bicarbonate to remove TFA salts to provide 2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)-N-(cyclopropylmethyl)nicotinamide as a white powder. MS (ESI, pos. ion) m/z: 417 (M+1). IC50 (uM) +++.

1. stirringto stir overnight
2. extractionextracted with DCM (3×10 mL)
3. extractionThe organic extract
4. washwas washed with water (1×10 mL), saturated sodium chloride (1×10 mL), saturated sodium bicarbonate (1×10 mL)
5. dry with materialdried with magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by reverse-phase preparative HPLC
9. customover 15 min
10. extractionextracted with saturated sodium bicarbonate
11. customto remove TFA salts

ORDレコード

ord-86e9ad33f6294e9d8b02d45fb355c40f

出典データセット

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08759532B2