2-(TRIFLUOROMETHYL)-4-HYDROXYPYRIDINE

Step F4-{[3-chloro-5~cyclopropyl-7-(trifluoromethyl)pyrazolo[1, 5-a]pyr^^methytcyclopentyi)-2-piperazinone[00194] A solution of 3-chloro-5-cyclopropyl-7-(trifluorometliyl)pyrazolo[l , 5-a]pyridine-2~ carboxylic acid (0.092 g, 0.302 mmol) and l-(3-methylcyclopentyl)-2-piperazinone FICl (.060 g, 0.274 mmol) in DMF (3.07 ml) was treated by the addition of HATU (0.115 g, 0.302 mmol) and DIPEA (0.120 ml, 0.686 mmol). The reaction mixture was stirred at room temperature for 2 hours and diluted with EtOAc and water. The combined organic phases were washed with 5percent LiCl (3x), saturated NaHC(3/4, brine, dried (MgS0A mixture of 2-(chloromethyl)-6-phenoxybenzo[d]oxazole (260 mg, 1 mmol), 2- (trifluoromethyl)pyridine-4-ol (163 mg, 1 mmol) and K2CO3 (138 mg, 1 mmol) in DMF (10 mL) was stirred overnight at rt. Excess solvent was evaporated under reduced pressure and to the remaining residue water (30 ml) was added and then extraction with DCM. The organic solvent was then dried over anhydrous MgS04 and evaporated under reduced pressure. The residue was purified by prep-HPLC using acetonitrile and water as eluent to afford the desired compound. 'H NMR (300 MHz, Acetone) d 8.61 (d, J = 5.7 Hz, 1H), 7.73 (d, 8.7 Hz, 1 H), 7.57 (d, J= 2.4 (0694) Hz, 1 H), 7.44 - 7.33 (m, 3H), 7.28 (d, J = 2.2 Hz, 1H), 7.20 - 7.12 (m, 1H), 7.10 (dd, J = 8.7, 2.3 Hz, 1H), 7.08 - 7.01 (m, 2H), 5.68 (s, 2H). LC.MS: m/z 387.13 (M+H)+.A mixture of 2-(bromomethyl)-5, 6-dichloro-lH-benzo[d]imidazole (1 10 mg, 0.39 mmol), 2- (trifluoromethyl)pyridine-4-ol (77 mg, 0.47 mmol) and CsC03 (153 mg, 0.47 mmol) in DMF (10 mL) was stirred at 60 C for lh. Excess solvent was evaporated under reduced pressure and to the remaining residue water (30 ml) was added and then extraction with DCM. The organic solvent was then dried over anhydrous MgS04 and evaporated under reduced pressure. The residue was purified by prep-HPLC using acetonitrile and water as eluent to afford the desired compound. NMR (300 MHz, Acetone) d 7.92 (d, J = 7.8 Hz, 1H), 7.78 (s, 2H), 6.66 (d, J = 2.8 Hz, 1 H), 6.35 (dd, J= 7.8, 2.8 Hz, 1 H), 5.62 (s, 2H). LC.MS: m/z 362.09 (M+H)+.A mixture of

Molecular Weight:163.10
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:163.02449824
Monoisotopic Mass:163.02449824
Topological Polar Surface Area:29.1
Heavy Atom Count:11
Complexity:239
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes