Pyrrole-2-Carboxylic Acid → HCID 59451446, compound

HATU (0.16 g, 0.43 mmol) was added to a solution of 3-chloro-5-({6-chloro-2-fluoro-3-[(methylamino)methyl]phenyl}oxy)benzonitrile (0.10 g, 0.30 mmol) and 1H-pyrrole-2-carboxylic acid (0.05 g, 0.43 mmol) in DMF (3 mL) and the solution was stirred at RT overnight. After 16 h, ethyl acetate (100 ml) and saturated NaHCO3 solution (100 ml) were added. The organic layer was separated, washed with saturated NaHCO3 solution (2×100 ml), brine (150 mL), dried over MgSO4, filtered and concentrated. The crude material was purified by Reverse Phase HPLC to give the title compound (0.042 g, 33%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.77 (d, 1H), 7.34-7.40 (m, 1H), 7.21-7.33 (m, 3H), 7.17 (t, 1H), 7.01-7.05 (m, 1H), 6.99 (d, 1H), 6.28 (d, 1H), 4.85 (br. s., 2H), 3.33 (br. s., 3H).

1. waitAfter 16 h
2. customThe organic layer was separated
3. washwashed with saturated NaHCO3 solution (2×100 ml), brine (150 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was purified by Reverse Phase HPLC

ORD record

ord-c77eb06b6fc147d89631cd8056051fbc

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2