6-Aminopyridine-2-carboxylic acid ethyl ester

To a solution of 2-amino-6-pyridinecarboxylic acid (90; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOClExample 6. Synthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(2- (trifluoromethyl)phenyl)benzo[d]oxazole-7-carboxamide (Compound 125) : Step 1) Preparation of ethyl 6-aminopicolinate (20): 19 20To a solution of 2-amino-6-pyridinecarboxyric acid (19; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOClStep 1. Preparation of ethyl 6-aminopicolinate (78):To a solution of 2-amino-6-pyridinecarboxylic acid 77 (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 Example 3. Preparation of 2-(4-fluoro-2-(trifluoromethyl)phenyl)-N-(6- (morpholinomethyl) pyridine-2-yl)-3H-imidazo[4, 5-b]pyridine-7-carboxamide (Compound 110):; Step 1) Synthesis of ethyl 6-aminopicolinate (10): 9 10To a solution of 2-amino-6-pyridinecarboxylic acid (9; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOClTo a solution of 2-amino-6-pyridinecarboxylic acid (64; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOClStep 1. Preparation of ethyl 6-aminopicolinate:To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOClTo a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 °C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temp, the reaction mixture was concentrated under reduced pressure. Saturated aqueous NaStep 1) To a solution of 2-amino-6-pyridinecarboxylic acid (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 °C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temp, the reaction mixture was concentrated under reduced pressure. Saturated aqueous NaSynthesis of N-(6-(morpholinomethyl)pyridin-2-yl)-2-(3- (trifluoromethyl)phenyl) imidazo[l, 2-a]pyridine-8-carboxamide (Compound 159): Step 1) Preparation of ethyl 6-aminopicolinate (43): 42 43 To a solution of 2-amino-6-pyridinecarboxylic acid (42; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl(4) Ethyl imidazo[1, 2-a]pyridine-5-carboxylate Ethyl 6-aminopyridine-2-carboxylate (2.6 g) was dissolved in ethanol (100 mL). Sodium carbonate (2.5 g) and chloroacetaldehyde (40% aqueous solution) (15 mL) were sequentially added and the mixture was heated under reflux for seven hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The drying agent was removed by filtration and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to obtain the title compound (2.39 g). 1H-NMR (400 MHz, CDCl3) delta(ppm): 1.46 (t, J=7.2 Hz, 3H), 4.48 (q, J=7.2 Hz, 2H), 7.23 (dd, J=7.2 Hz, 8.8 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.80 (d, J=7.2 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H) , 8.82-8.85 (m, 1H).Example 62 Synthesis of ethyl 2-(chloromethyl)imidazo[1, 2-a]pyridine-5-carboxylate. A mixture of (4-Bromophenyl)acetylene 1a (72.4 mg, 0.40 mmol) was sequentially added to a 15 mL Schlenk reaction tube under an atmospheric pressure of oxygen.2-Bromomethylthiophene 2a (35.4 mg, 0.20 mmol),

Molecular Weight:166.18
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:166.074227566
Monoisotopic Mass:166.074227566
Topological Polar Surface Area:65.2
Heavy Atom Count:12
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes