Cyclohexylamine → HCID 18446572, Verbindung

To a solution of 4-chloro-7-cyano-2-(4′-t-butylphenyl)-thieno[3,2-c]pyridine (0.05 g, 0.153 mmol) in DMF was added cyclohexylamine (0.017 g, 0.168 mmol) and potassium carbonate (0.023 g, 0.168 mmol). The resulting mixture was stirred under nitrogen at 80° C. for 2 h. After this time the mixture was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL), and the organic layer washed with water and brine, then dried over magnesium sulphate and concentrated under reduced pressure. Purification by silica gel chromatography (eluent 20% ethyl acetate in hexane) afforded 0.042 g of 102. 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.63 (d, 2H), 7.50 (d, 2H), 7.38 (s, 1H), 5.14 (bs, 1H), 4.20 (bs, 1H), 2.18 (m, 2H), 1.80 (m, 4H), 1.6-1.12 (m, 13H).

1. customAfter this time the mixture was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL)
2. washthe organic layer washed with water and brine
3. dry with materialdried over magnesium sulphate
4. concentrationconcentrated under reduced pressure
5. customPurification by silica gel chromatography (eluent 20% ethyl acetate in hexane)

ORD-Eintrag

ord-bc022de74c424f57998adcaf49bb0208

Quelldatensatz

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07635695B2