6-Methoxy-3-nitro-2-pyridinamine

Yellow solid

6- [({2- [6-(methyloxy)-3-oxopyrido [2, 3-b] pyrazin-4(3H)-yl] -5, 6, 7, 8- tetrahydro-6-quinazolinyl}amino)methyl]-2H-pyrido[3, 2-b][l, 4]oxazin-3(4H)-one hydrochloride; (a) 6-(Methyloxy)-3 -nitro-2-pyridinamine; A solution/suspension of 2-chloro-6-(methyloxy)-3-nitropyridine (65.7 g, 348 mmol) in 2M ammonia in methanol (500 ml, 1000 mmol) and aqueous ammonia (500 ml, 348 mmol) was stirred at 65°C for 18h. The reaction was cooled down and the solid filtered off and washed with water (2x100ml). The solid was dried in the vacuum oven at 4OExample 13A; (lR)-l-({4-[([l, 3]Oxathiolo[5, 4-c]pyridin-6-ylmethyl)amino]-l- piperidinyl}methyl)-l, 2-dihydro-3H, 8H-2a, 5, 8a-triazaacenaphthylene-3, 8-dione hydrochloride; Preparation '6-Methoxy-3-nitro-2-pyridineamine [Formula 50]; A solution of 2-chloro-6-methoxy-3- nitropyridine (25.3 g, 0.134 mol) and a concentrated aqueous ammonia solution (70 ml) in N, N- dimethylformamide (200 ml) was stirred at 70°C for 4 hours and 15 minutes. The reaction mixture was cooled to room temperature and then diluted with water. The resulted precipitate was collected by filtration to yield the title compound (16.8 g, 99.2 mmol, 74.0percent) as a yellow solid. A. Sodium methoxide, 7.78 gm (0.144 mole) and methanol 50.0 ml were mixed and cooled to 15° C. To a solution of 2-amino-3-nitro-6-chloropyridine (300 mg, 1.73 mmol, an intermediate in preparation of 8) in 5 mL anhydrous DMF was added sodium methoxide (187mg, 3.46 mmol). This mixture was stirred at room temperature for 3 h then poured onto 20 g crushed ice and extracted with ethyl acetate. The extracts were dried, evaporated and purified by column chromatography on silica gel (PE/AcOEt=5:1) to give 2-amino-3-nitro-6-methoxylpyridine (246 mg, 84.1percent) as yellow solid. Next steps followed the general procedure, and the title compound was obtained as white solid (188 mg, 67.0percent over 2 steps). IR (KBr) ν 3246, 3184, 1708, 1635, 1599, 1488, 1462, 1341, 1260, 1024, 839cmTo a stirred solution of Compound 39b (15g, 86.70mmol) in MeOH (35ml) was added NaOMe (7.2g, 133.92mmol) at -15°C and stirred for 16h at RT. The reaction was quenched with ice and the obtained solids were filtered and dried to afford the required compound (9g).

Used as an intermediate for drug tetazol

Molecular Weight:169.14
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:169.04874109
Monoisotopic Mass:169.04874109
Topological Polar Surface Area:94
Heavy Atom Count:12
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes