2-AMINO-6-BROMOTHIAZOLO[4,5-B]PYRAZINE

To a suspension of ethyl 6-bromothiazolo[4, 5-b]pyrazin-2-ylcarbamate 73 (480 mg, 1.58 mmol) in methanol (8 ml) was added 2N sodium hydroxide aqueous solution (7.91 ml, 15.83 mmol). It was heated for 5 hours under reflux. After the end of the reaction, the mixture was acidified with 2N HCl. Then the mixture was neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and saturated NaCl aqueous solution and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The precipitate was collected by filtration to give Compound 74 (334 mg, yield 91.0 percent) as a white yellow solid. Reference Example 444 6-bromo-2-(2, 5-dimethyl-1H-pyrrol-1-yl)[1, 3]thiazolo[4, 5-b]pyrazine A mixture of To a suspension of 6-bromothiazolo [5, 4-b] pyrazin-2-amine (700 mg, 3.03 mmol) in DMF (3 ml)16.0 M sodium hydroxide (400 mul, 6.40 mmol) was added. The mixture was stirred at room temperature for 10 minutes at which time carbon disulfide (450 mul, 7.57 mmol) was added and the resulting reddish brown mixture was stirred for 10 minutes. A further 16.0 M sodium hydroxide (400 mul, 6.40 mmol) was added and the mixture was again stirred for 10 min. Finally, iodomethane (450 mul, 7.27 mmol) was added dropwise. The mixture was stirred for 5 minutes at which time a large amount of yellow precipitate formed. The mixture is poured into water and the solid is collected by filtration to give dimethyl 6-bromothiazolo [5, 4-b] pyrazin-2-ylcarbonimidodithioate as a yellow solid of sufficient purity to be used without further purification (680 mg, yield 67%).To a suspension of ethyl 6-bromothiazolo[4, 5-b]pyrazin-2-ylcarbamate 73 (480 mg, 1.58 mmol) in methanol (8 ml) was added 2N sodium hydroxide aqueous solution (7.91 ml, 15.83 mmol). It was heated for 5 hours under reflux. After the end of the reaction, the mixture was acidified with 2N HCl. Then the mixture was neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and saturated NaCl aqueous solution and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The precipitate was collected by filtration to give Compound 74 (334 mg, yield 91.0 %) as a white yellow solid. 1H-NMR (DMSO-d6) delta: 8.37 (s, 1H), 8.59 (brs, 2H).

Molecular Weight:231.08
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Exact Mass:229.92618
Monoisotopic Mass:229.92618
Topological Polar Surface Area:92.9
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes