4-Bromo-2,6-pyridinediamine

Off-white solid

c) 4-Bromo-pyridine-2, 6-diamine A suspension of 1 g (3.65 mmol) 4-bromo-pyridine-2, 6-dicarboxylic acid dihydrazide in 32 ml water was treated with 1.6 ml HCl (37percent) at room temperature. The resulting mixture was cooled to 0° C. and 554 mg NaNO2 in 2.4 ml water was added slowly maintaining the temperature below 2° C. Upon completion saturated NaHCO3 solution was added to pH 8 and the white precipitate was filtered off and washed with water. The residue was dissolved in CHCl3 and dried with MgSO4. The filtrate was concentrated at 20° C. to yield 920 mg (85percent) of a white solid 450 mg (1.5 mmol) of the white residue were suspended in toluene/t-butanol 5/1. After refluxing for 12h the solvent was removed under reduced pressure and 5 ml toluene and 0.3 ml trifluoroacetic acid were added and refluxed for 2 h. The solvents were removed and the residue was purified by flash chromatography on silica eluting with dichloromethane/methanol 9/1. After removal of the solvents the title compound was liberated through addition of 1N NaOH to a suspension of the residue in diethylether. The organic phase was dried with Na2SO4 and the solvents removed under reduced pressure yielding 192 mg (67percent) of the desired product, MS m/e (percent): 188 (M+, 100).Bromine (0.2 ml) was added drop wise to a KOH solution (5M, 20 mL) at 0C and reaction mixture was stirred at 0C. After lh, 4-Bromopyridine-2, 6- dicarboxamide (4.1 g, 0.017 mol) was added slowly to the reaction mixture at 0C and stirred for 30 mi Further, the reaction mixture was heated 90C for2h. After consumption of starting materials (TLC), the reaction mixture was extracted with ethyl acetate (5x100 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The crude was washed with hexane, filtered and dried under vacuum to afford the desired 4- Bromopyridine-2, 6-diamine, which was taken to the next step without furtherpurification (1.86 g.)HPLC-MS (method C): Rt= 0.8 mm, [M+H] mlz: 190.Yield: not purified.EXAMPLE 85 7-Bromo-2-(5-methoxy-thiophen-2-yl)-[1, 2, 4]triazolo[1, 5-a]pyridin-5-ylamine The title compound, MS m/e (%): 325 (M+, 100), was prepared in accordance with the general method of example 63 from EXAMPLE 65 7-Bromo-2-(5-methyl-furan-2-yl)-[1, 2, 4 ]triazolo 1, 5-a]pyridin-5-ylamine The title compound, MS m/e (%): 295 (M++2, 100), was prepared in accordance with the general method of example 63 from EXAMPLE 70 7-Bromo-2-thiophen-2-yl-[1, 2, 4]triazolo[1, 5-a]pyridin-5-ylamine The title compound, MS m/e (%): 297 (M++2, 100), was prepared in accordance with the general method of example 63 from EXAMPLE 64 7-Bromo-2-furan-2-yl-[1, 2, 4]triazolo[1, 5-a]pyridin-5-ylamine The title compound, MS m/e (%): 281 (M++2, 100), was prepared in accordance with the (general method of example 63 from

Molecular Weight:188.03
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:186.97451
Monoisotopic Mass:186.97451
Topological Polar Surface Area:64.9
Heavy Atom Count:9
Complexity:88.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes