6-Chloro-N-methylnicotinamide

Preparation of 5-(6-ethoxypyridin-3-yl)-3-(3-(4-(1, 1, 1, 3, 3, 3-hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy) benzyl)-5-methylimidazolidine-2, 4-dione; 13-a-1) Preparation of 6-chloro-N-methylnicotinamide; To a solution of 6-chloro-N-methylnicotinoyl chloride (7.39 g, 42.0 mmol) in tetrahydrofuran (50 mL), methylamine (42 mL, 84.0 mmol) and triethylamine (6.4 mL, 46.2 mmol) were added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was concentrated in vacuo, then filtered, and washed with tetrahydrofuran. The obtained residue was recrystallized (ethyl acetate/hexane) and 6-chloro-N-methylnicotinamide (6.52 g, yield 91percent) was obtained as a white crystal.Example 100 To a stirred solution of β-chloropyridine-S-carbonyl chloride (1.5 g, 8.52 mmol) in DCM (10 ml) at OThionyl chloride (3.48 mL, 47.7 mmol) and DMF (2 drops) were added with stirring to a solution of 6-chloropyridine-3-carboxylic acid (3.0 g, 19.1 mmol) in toluene (15 mL) at rt. The mixture was heated and stirred at 100 °C for 2.5 h, then cooled and concentrated in vacuo to afford 6-chloropyridine-3-carbonyl chloride. The carbonyl chloride dissolved in CHA mixture of 6-chloronicotinic acid methyl ester(10.0 g, 58.3 mmol) was dissolved in 10 mL of methanol and stirred to form a pale yellow solution. A 40percent aqueous solution of methylamine (2.7 g, 87.5 mmol) was added dropwise at 0 ° C, and the reaction was carried out at room temperature for 4 h The The filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, crystallized, filtered and dried to give 9.4 g of pale yellow crystals, and the residue was washed with water, Yield 99.1percent. Μρ: 140-142 ° C.6-chloronicotinic acid methyl ester (10.0g, 58.3mmol) was dissolved in 10mL 52 methanol to get light yellow solution, the 14 methylamine (2.7g, 87.5mmol) in 53 water solution was added dropwise at 0–5°C under stirring. The mixture was stirred at room temperature for 4h, and then concentrated in vacuum. Finally, 54 ethyl acetate (100mL) was added, and the resulting mixture was stirred at room temperature. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give light yellow crystalline (2) 9.4g, yield: 99.1percent, mp: 145–146°C.

Molecular Weight:170.59
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:170.0246905
Monoisotopic Mass:170.0246905
Topological Polar Surface Area:42
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes