6-Chloro-2,3-diaminopyridine

Dark green solid

A mixture of 6-chloro-2-nitropyridin-3-amine (E-23) (8.8 g, 51 mmol, 1.0 eq) and Raney nickel (0.88 g) in Methanol (100 mL) was stirred under hydrogen at RT for 24h, then filtered and the filtrate was concentrated in vacuo to afford the desired product 6-chloropyridine-2, 3 -diamine (E-24) (7g, 95.6percento yield ) as a pale solid. ESI-MS m/z : 144.05[M+H][00326] A mixture of 6-chloro-2-nitropyridin-3-amine (E-23) (8.8 g, 51 mmol, 1.0 eq) and Raney nickel (0.88 g) in Methanol (100 mL) was stirred under hydrogen at RT for 24h, then filtered and the filtrate was concentrated in vacuo to afford the desired product 6-chloropyridine-2, 3-diamine (E-24) (7g, 95.6percent yield ) as a pale solid. ESI-MS m/z : 144.05[M+H]a) 6-Chloropyridine-2, 3-diamine (A45) Iron powder (9.65 g, 173 mmol) was added to a suspension of 6-chloro-3-nitropyridin-2- amine A44 (10.0 g, 57.6 mmol) and NHGeneral procedure: SAC (300mg) and NaBHCompound 1 (500 g, 2.89 mol), Ammonium chloride (300 g, 5.75 mol) was dissolved in 5000 ml of ethyl acetate and 3000 ml of water, To this mixture was added iron powder (482.5g, 8.65mol) at room temperature, the reaction was carried out at room temperature for 4 hours, The reaction was complete by TLC and the reaction mixture was filtered. The filtrate was separated and the aqueous phase was extracted twice with 1500 ml of ethyl acetate. The combined organic phases were dried over saturated brine and concentrated to give compound 2 (370 g, 2.58 mol)Yield 89.2percentIntermediate 16-Chloropyridine-2, 3-diamineIn a 2-neck, 250 mL glass round bottom flask 6-chloro-3-nitropyridin-2-amine (J Med. Chem., 2000, 43, 3053-3066, 5 g, 28.81 mmol) and tin (II) chloride dihydrate (32.5 g, 144.04 mmol) were combined and suspended in EtOAc (90 mL) and (10 mL).The reaction slurry was heated to 6OTo a mixture of ethyl acetate (450 mL) and tert-butanol (50 mL), 6-chloro-3- nitropyridin-2-amine (CAS 27048-04-0) (15g, 86, 42 mmol), stannous chloride dehydrate (CAS 10025-69-1) (97.5 g, 432.1 mmol) were added. The resulting mixture was stirred at 60°C for 1 hour. Sodiumborohydride (1.63 g, 43.21 mmol) was added and the mixture was stirred further at 60°C for another 3h. The mixture was cooled and stripped from the EtO Ac on the rotavapor. The resulting residu was diluted with water (350 mL) and neutralized to pH = 9-10 by addition of an aqueous solution of potassium carbonate. The resulting mixture was extracted with EtO Ac (3x 250 mL), dried over NaTo a mixture of ethyl acetate (450 mL) and tert-butanol (50 mL), 6-chloro-3-nitro- pyridin-2-amine (15 g, 86, 42 mmol), stannous chloride dehydrate (97.5 g, 432.1 mmol) were added. The resulting mixture was stirred at 60°C for 1 hour. Sodiumborohydride (1.63 g, 43.21 mmol) was added and the mixture was stirred further at 60°C for another 3h. The mixture was cooled and stripped from the EtO Ac on the rotavapor. The resulting residu was diluted with water (350 mL) and neutralized to pH = 9-10 by addition of an aqueous solution of potassium carbonate. The resulting mixture was extracted with EtO Ac (3x 250 mL), dried over NaTo a mixture of ethyl acetate (450 mL) and fert-butanol (50 mL), 6-chloro-3- nitropyridin-2-amine (CAS 27048-04-0) (15g, 86, 42 mmol), stannous chloride dehydrate (CAS 10025-69-1) (97.5 g, 432.1 mmol) were added. The resulting mixture was stirred at 60°C for 1 hour. Sodiumborohydride (1.63 g, 43.21 mmol) was added and the mixture was stirred further at 60°C for another 3h. The mixture was cooled and stripped from the EtO Ac on the rotavapor. The resulting residu was diluted with water (350 mL) and neutralized to pH = 9-10 by addition of an aqueous solution of potassium carbonate. The resulting mixture was extracted with EtO Ac (3x 250 mL), dried over NaIntermediate 4.1: 6-Chloro-pvridine-2, 3-diamine (Scheme 10); 2-arnino-3-nitro-6-chloropyridine (3 g, 17.3 mmol, 1 eq.) was dissolved in THF (50 mL) at it. Tin chloride dihydrate (15.6 g, 70 mmol, 4 eq.) pre-dissolved with HClcc (5 mL) was added slowly and reaction mixture stirred at rt for 4 hours. When thereaction was finished, reaction mixture was cooled down to 0°C and treated with sodium hydroxide 5M (12 mL) until pH 14 and the corresponding compound extracted with ethyl acetate. Organic phases were dried with magnesium sulfate, evaporated under vacuum and resulting crude material purified by flash chromatography using cyclohexane/ethyl acetate (1/1) to give 1.5 g of a red oil (Intermediate 4.1). Amount: 1.5 g; Yield: 60 percent; Formula: CStep 1 - Synthesis of N

Molecular Weight:143.57
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:143.0250249
Monoisotopic Mass:143.0250249
Topological Polar Surface Area:64.9
Heavy Atom Count:9
Complexity:98.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes