Diisopropylethylamine → HCID 68485337, compound

DIPEA (0.20 mL, 1.16 mmol) was added to a mixture of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.15 g, 0.48 mmol), 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid (0.080 g, 0.58 mmol) and HATU (0.24 g, 0.63 mmol) in DMF (3 mL). The yellow solution was stirred at RT under nitrogen for 24 h then ethyl acetate (50 mL) and saturated sodium bicarbonate solution (100 mL) was added. The organic layer was separated, washed with saturated sodium bicarbonate solution (50 mL), water (50 mL), brine (50 mL) and dried over MgSO4. The mixture was filtered and the solvent was removed under vacuum. The crude material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA) to give the title compound (0.20 g, 10%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.42 (br. s., 1H), 9.75 (br. s., 1H), 7.74-7.95 (m, 2H), 7.42-7.57 (m, 3H), 7.37 (t, 1H), 4.44 (d, 2H), 2.20 (s, 3H). LCMS m/z 437.0 (M+H).

1. customThe organic layer was separated
2. washwashed with saturated sodium bicarbonate solution (50 mL), water (50 mL), brine (50 mL)
3. dry with materialdried over MgSO4
4. filtrationThe mixture was filtered
5. customthe solvent was removed under vacuum
6. customThe crude material was purified by Reverse Phase HPLC (MeCN/water+0.1% TFA)

ORD record

ord-cb378c72989e4821a19e2ab29970c94c

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2