2-Amino-5-Acetylpyridine

Step 4 1-(6-Aminopyridin-3-yl)ethanone: Into a 1 L high pressure clave, was placed a solution of 1-(6-chloropyridin-3-yl)ethanone (40 g, 257.10 mmol) in saturated ammonium (750 ml). The reaction mixture was stirred at 130° C. for 10 h. The mixture was cooled and concentrated under reduced pressure. The residue was purified by silica gel chromatography (50:1 CHStep A: 1-(6-Aminopyridin-3-yl)ethanone (16) [00379] A solution of 1-(6-chloropyridin-3 -yl)ethanone ( 15) (2 g, 13 mmol) in HExample 37 N-(5-Acetyl-pyridin-2-yl)-3-[7-fluoro-2-(4-fluoro-benzyl)-3-oxo-2, 3-dihydro-1H-isoindol-1-yl]-propionamide A. 1-(6-Aminopyridin-3-yl)-ethanone; 1-(6-Chloropyridin-3-yl)-ethanone (230 mg, 1.5 mmol), 1 mL 28percent aq NH2 g (11.57 mmol) of 1-(6-chloropyrid-3-yl)ethanone and 70 mL of ammonium hydroxide are placed in a Parr reactor. The solution is heated at 130°C overnight. The mixture obtained is evaporated to dryness, and the residue is taken up in ethyl acetate and washed with water and with saturated NaCl solution. The organic phase is dried over sodium sulfate and evaporated to dryness to give 1.14 g of 1-(6-aminopyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 137. tr (min) = 0.35. 2 g (11.57 mmol) of 1-(6-chloropyrid-3-yl)ethanone and 70 mL of ammonium hydroxide are placed in a Parr reactor. 6-Aminonicotinic acid (9, 5.5 g 40 mmol), N, N'-carbonyldiimidazole (CDI, 6.6 g 40.8 mmol) was dissolved in 200 mL of DMF, stirred at 70 C for 1 hour, and ethyl pyridine (10, 4.6 g 40 mmol), react for 6 hours. The reaction was stopped, rotary evaporation, ethyl acetate / water (100 mL / 100 mL) was stirred and extracted, the organic phase was collected, dried over anhydrous sodium sulfate, and rotary evaporation to give a yellow solid 11 (7.8 g, 83%).Step A: 2-(6-Aminopyridin-3-yl)-6-chloroquinoline-4-carboxylic acid (27) [00392] A solution of l-(6-aminopyridin-3-yl)ethanone 16, example 8, step A) (1.5 g, 11.0 mmol) in ethanol (10 mL) was added slowly to a solution of 5-chloroindoline-2, 3-dione (9) (1.66 g, 9.17mmol) in 6M aqueous KOH (lOmL) at 100C. The reaction was monitored by LCMS until the staring material consumed. Then the reaction mixture was concentrated to remove ethanol, the residue was diluted with water (10 mL), the pH value of the mixture was acidified to 5 by adding 1M aqueous HCl solution. The precipitate was filtered to give the desired product (1.2 g, 44%) as an orange solid. LC-MS: (M + H)+ 300.1Step B: 2-(6-Aminopyridin-3-yl)-8-chloroquinoline-4-carboxylic acid (17) [00380] A solution of l-(6-aminopyridin-3-yl)ethanone (16, step A) (1.5 g, 11.0 mmol) in ethanol (10 mL)was added slowly to a solution of 7-chloroindoline-2, 3-dione (4) (1.66 g, 9.17mmol) in 6M aqueous KOH (lOmL) at 100C. The reaction was monitored by LCMS until the staring material consumed. Then the reaction mixture was concentrated to remove ethanol, the residue was diluted with water (10 mL), the pH value of the mixture was acidified to 5 by adding 1M aqueous HC1 solution. The precipitate was filtered to give the desired product (1.2 g, 44%) as an orange solid. LC-MS: (M + H)+ 300.1

Molecular Weight:136.15
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:136.063662883
Monoisotopic Mass:136.063662883
Topological Polar Surface Area:56
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes