5-CHLORO-3H-IMIDAZO[4,5-B]PYRIDINE

Compound 2 (350 g, 2.44 mol) and p-toluenesulfonic acid monohydrate (46.5 g, 0.244 mol) were added to triethyl orthoformate (2100 g, 14.2 mol) and refluxed for 5 hours.After completion of the reaction by TLC, the reaction solution was concentrated and the crude product was quickly purified by column to give Compound 3 (222 g, 1.45 mol). (Yield 59percent) NMR spectrum is shown in FIG. 2.Compound 2 (350 g, 2.44 mol) and p-toluenesulfonic acid monohydrate (46.5 g, 0.244 mol) were added to triethyl orthoformate (2100 g, 14.2 mol) and refluxed for 5 hours.After completion of the reaction by TLC, the reaction solution was concentrated and the crude product was quickly purified by column to give Compound 3 (222 g, 1.45 mol). (Yield 59percent) NMR spectrum is shown in FIG. 2.5-Chloro[4, 5-b]pyridine (207 mg, 1.1 mmol, 1 eq), DavePhos (10 mg, 0.0264 mmol, 0.25 eq) and Pd2(dba)3 (9 mg, 0.011 mmol, 0.1 eq) were dissolved in dry THF (15 ml) under Argon atmosphere. LiN(TMS)2 (1 M in THF, 2.4 ml, 2.4 mmol, 2.2 eq) and benzylamine (144 pi, 1.3 mmol, 1.2 eq) were added and the mixture was stirred at 65C for 18 h. After cooling to room temperature the mixture was acidified by means of aqueous HCI (5 N) and stirring was continued for further 10 min. The reaction mixture was poured into saturated aqueous NaHCCb and extracted with EtOAc (3x25 ml). The combined organic layers were dried over MgCCb and evaporated to dryness. The residue was purified by semi-preparative HPLC. Yield: 90 mg (24%); MS m/z: 225.2 [M+H]+; HPLC (Gradient A): rt 8.93 min, 100 %; 1H-NMR (DMSO-d6) d: 4.55 (s, 2H); 6.80 (d, 1 H, 3J=8.8 Hz); 7.22-7.27 (m, 1 H); 7.30-7.37 (m, 4H); 7.83-7.91 (m, 2H); 9.08 (s, 1 H)Compound 3 (200 g, 1.3 mol) was dissolved in 1500 ml of acetic acid and then m-chloroperoxybenzoic acid (448.5 g, 2.6 mol) was added and reacted at room temperature for 6 hours.After completion of the reaction by TLC, the reaction mixture was filtered, and the residue was washed with ether to give crude compound 4 (220 g). (Yield 99%)Example 209To a 1:1 mixture (lOOmg) of 7-chloro-lH-imidazo [4, 5-b] pyridine and 5-chloro-lH-imidazo [4, 5-b] pyridine was addedN-methylcyclohexanamine (500 ul) , and irradiated microwave at 2000C for 2hours . The reaction mixture was diluted with chloroform, washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography over NH-silica gel with a chloroform / EtOAc (100:1-100:5) as eluant to give N-cyclohexyl-N-methyl- EPO Stage B Compound 2 (350 g, 2.44 mol) and p-toluenesulfonic acid monohydrate (46.5 g, 0.244 mol) were added to triethyl orthoformate (2100 g, 14.2 mol) and refluxed for 5 hours.After completion of the reaction by TLC, the reaction solution was concentrated and the crude product was quickly purified by column to give Compound 3 (222 g, 1.45 mol). (Yield 59%) NMR spectrum is shown in FIG. 2.A solution of 6-Chloropyridine-2, 3-diamine (718 mg, 5 mmol) in Methanol (10 ml) and Trietyhl orthoformate (10 ml) was heated to reflux for 3 hours. The volatiles were evaporated and the residue was purified by flash chromatography on silica using a CHCl3-MeOH gradient. Yield: 540 mg (58%); ESI-MS m/z 151.1 [M+H]+

Molecular Weight:153.57
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:153.0093748
Monoisotopic Mass:153.0093748
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes