Pyridine → N-(4-tert-Butylphenyl)-1-(3-(trifluoromethyl)pyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

To a suspension of 3′-trifluoromethyl-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (60.4 mg, 0.194 mmol) and DMF (cat) in CH2Cl2 (1 mL) was added (COCl)2 (0.027 mL, 0.31 mmol). The mixture was stirred for 90 minutes, diluted with PhMe (0.5 mL), concentrated under reduced pressure to dryness, and dissolved in CH2Cl2 (1.5 mL). To the solution were added pyridine (0.027 mL, 0.33 mmol), DMAP (cat), and 4-tert-butylaniline (0.037 mL, 0.023 mmol). The mixture was stirred 1 hour, diluted with water and extracted with CH2Cl2, dried (Na2SO4), and purified by flash chromatography (7% EtOAc/CH2Cl2) to provide as a white solid (54.2 mg, 0.123 mmol, 63%): MS (ESI+) m/z 404 (M+H)+, m/z 402 (M−H)−; 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.31 (s, 9 H), 2.67 (m, 2 H), 3.53 (t, J=5.4 Hz, 2 H), 4.07 (q, J=2.9 Hz, 2 H), 6.67 (m, 1 H), 6.98 (dd, J=7.5, 4.4 Hz, 1 H), 7.36 (m, 3 H), 7.48 (m, 2 H), 7.89 (dd, J=7.8, 1.7 Hz, 1 H), 8.42 (dd, J=4.7, 1.4 Hz, 1 H).

1. concentrationconcentrated under reduced pressure to dryness
2. dissolutiondissolved in CH2Cl2 (1.5 mL)
3. stirringThe mixture was stirred 1 hour
4. extractionextracted with CH2Cl2
5. dry with materialdried (Na2SO4)
6. custompurified by flash chromatography (7% EtOAc/CH2Cl2)

ORD-Eintrag

ord-b91ab07b7cb44c69830759d677988ef6

Quelldatensatz

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07129235B2