Hydrochloric Acid → HCID 86632134, compound

The HCl salt (obtained from step 1 above) was dissolved in DMF (15 mL) and transferred to a flask containing a solution of 6-chloropicolinic acid (1.0 g, 6.3 mmol), and HATU (2.9 g, 7.6 mmol) in DMF (10 mL). N-Methylmorpholine (1.5 mL, 1.38 g, 13.6 mmol) was then added and the resulting reaction mixture was allowed to stir at room temperature under N2 atmosphere overnight. The heterogeneous reaction mixture was then poured into saturated sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were then washed with water (2×50 mL), brine (1×50 mL), dried (MgSO4), filtered and concentrated to give a brown residue, which upon trituration with ethyl ether provided 6-chloro-N-(1-(pyridin-4-ylmethyl)piperidin-4-yl)picolinamide as a yellow crystalline solid (1.31 g, 64%). 1H NMR (CDCl3) δ 8.93-8.82 (m, 2H), 8.12-8.06 (m, 1H), 7.96-7.74 (m, 5H), 7.51-7.47 (m, 1H), 4.34 (br s, 2h), 4.26 (br s, 1H), 3.63-3.47 (m, 2H), 3.16-2.92 (m, 2H), 2.60-2.40 (m, 2H), 2.36-2.14 (m, 2H). MS (m/z): 331 (M+H)+ confirmed by LC-MS, tr=3.67 min

1. customtransferred to a flask
2. customthe resulting reaction mixture
3. extractionextracted with ethyl acetate (3×50 mL)
4. washThe combined organic layers were then washed with water (2×50 mL), brine (1×50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a brown residue, which upon trituration with ethyl ether

ORD record

ord-c353e60e7df94836a0a28eaa3fca72fe

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569340B2