3-METHOXY-2-PYRIDINECARBOXYLIC ACID

The reaction mixture of compound 5 (261 mg, 1.56 mmol), NaOH (281 mg, 7.03 mmol) in MeOH (9 mL) and water (6 mL) was stirred at rt for 1.5 h. The solvent was removed under reduced pressure and the residue was diluted with water. The solution was extracted with EtOAc (5 times). The organic phases were combined and evaporated under vacuum to give 6 as a light yellow solid. 1H NMR (300 MHz, CD3OD) delta 8.18 (s, 1H), 7.78 (d, J = 8.3 Hz, 1H), 7.67 (s, 1H), 3.96 (s, 3H).Compound 3-Methoxy-2-picolinic acid methyl ester (261 mg, 1.56 mmol), Sodium hydroxide (281 mg, 7.03 mmol) was dissolved in methanol (9 ml) and water (6 ml).Stir at room temperature for 1.5 hours. Spin down the solvent, add water to dissolve, Ethyl acetate was extracted 5 times, and the organic phases were combined and spin-dried to give the next reaction.N, N-Diisopropylethylamine (72 mI, 0.41 mmol) and HATU (1 18 mg, 0.310 mmol) were added to a solution of 6-phenoxybenzo[d]thiazol-2-amine (50 mg, 0.21 mmol) and [0355] A flask was charged with 3-amino-4-(4-(2, 4-difluorophenoxy)piperidin-l-yl)benzonitrile (15 mg, 0.046 mmol), General procedure: The mixture of ethyl 3, 4-diaminobenzoate 19 (1 eq., 7.34 mmol) and appropriate benzoic acid (1 eq., 7.34 mmol) was put under argon atmosphere and 15 mL of POCl3 were added. The whole was heated at reflux for 3 h. The mixture was cooled to room temperature, poured on ice and neutralized with 6 M NaOH (80 mL), then brought to pH ca. 9 by addition of 20 g of solid NaHCO3. 100 mL of CHCl3 were added and phases were separated. Aqueous phase was extracted with CHCl3 (2×50 mL). Combined organic phases were purified by chromatography on silica gel (CHCl3/MeOH, gradient 0'5 percent).

Molecular Weight:153.14
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:59.4
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes