Hydrochloric Acid → HCID 11698688, compound

Temperature

50 °C

Methyl N-({3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]biphenyl-4-yl}carbonyl)-L-valinate (84.2 mg, 0.17 mmol) was suspended in THF (2.5 mL), MeOH (2.5 mL) and water (1 mL), and LiOH (40.7 mg, 1.70 mmol) was added. The reaction mixture was heated at 50° C. for 2 h. Upon cooling to rt, the reaction mixture was brought to pH 3 with 1N HCl and was extracted with EtOAc (3×25 mL). The combined organic phases were washed with water (2×50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. This yielded 72.3 mg (88%) of the title compound as a white solid. LC/MS m/z 482.3 (MH+), retention time 3.46 min. 1H NMR (400 MHz, DMSO-d6) δ 0.99 (dd, 6H), 2.19-2.24 (m, 1H), 4.30 (dd, H), 7.18 (t, 1H), 7.60-7.84 (m, 6H), 7.88 (d, 2H), 8.42 (d, 1H), 8.66 (t, 1H), 10.42 (s, 1H).

1. temperatureUpon cooling to rt
2. extractionwas extracted with EtOAc (3×25 mL)
3. washThe combined organic phases were washed with water (2×50 mL) and brine (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-25a1c7a1f9694c71b12f24f99f47ed40

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759376B2