2-Amino-6-bromothiazolo[5,4-b]pyridine

A solution of N-(6-bromothiazolo[5, 4-b]pyridin-2-yl)benzamide III (2.0 g, 5.98 mmol) in 70percent HTo 1 -(2, 6-dibromopyridin~3-yl)thiourea (4.1 g, 13.2 mmol), which was dried under high vacuum and flushed with argon, were added caesium carbonate (8.59 g, 26.4 mmol), copper(i)iodide (126 mg, 0.66 mmol), DL-proiine (152 mg, 1 .3 mmol) and DMSO (94 mL). The mixture was stirred at room temperature while the addition of copper(l)iodide (42 mg, 0.22 mmol), DL-proline (51 mg, 0.44 mmol) and DMSO (5 mL) was repeated after 30, 60 and 90 minutes. After 2 hours the mixture was quenched with a saturated NH CI-solution ice water mixture and stirred for 5 minutes and then basified with aqueous ammonia to pH 8. The aqueous phase was multiple times extracted with a dichioromethane - methanol mixture (10: 1 ). The combined organic extracts were washed with brine, dried over sodium sulphate and evaporated under reduced pressure. The solid raw product was triturated with a hexane-dichloromethane mixture (10: 1 ) to yield 1 .6 g (51 percent) of 6-bromothiazolo[5, 4-b]pyridin-2-amine:1 H NMR (400 MHz, DMSO-cfe) δ = 7.42 (d, 1 H), 7.56 (d, 1 H), 8.00 (s, 2H) ppm.6-Bromo-[1 , 3]thiazolo[5, 4-b]pyridin-2-amine (0.1 g, 0.43 mmol) was dissolved in N-methyl-2-pyrrolidone (1.5 mE) and ethyl 3-bromo-2-oxopropanoate (64 pi, 0.43 mmol) added dropwise. The reaction was stirred at room temperature for 1 hour then heated to 60 C. overnight. The reaction was cooled then water/ice added. The resulting precipitate was isolated by vacuum filtration. The red solid was further dried in a vacuum oven to give the title compound. 'H NMR(500 MHz, DMSO) 9.05 (s, 1H), 8.95 (d, J=2.1 Hz, 1H), 8.74 (d, J=2.1 Hz, 1H), 4.32 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H). Tr(MS10)=1.55 mi mlz (ES(M+H)328, 329General procedure: The mixture of 6-bromobenzo[d]thiazol-2-amine (2.0 g, 8.73 mmol), carbonyldimidazole (4.24 g, 26.2 mmol) and dried DMF (20 ml) was stirred at room temperature for 8 h, added cyclopropanamine (0.76 g, 13.2 mmol), then stirred at room temperature for another 8 h. The volatile was removed under reduced pressure. Water (30 ml) was added to the residue. The resulting suspension was stirred. After standing, the solid was collected by filtration, dried to produce 8a (1.77 g, 65%) as white solid. 4.1.1.9 1-(6-Bromothiazolo[5, 4-b]pyridin-2-yl)-3-(2-(morpholinoethyl)urea (8i) White solid; Yield 86%; mp: 152-154 C; 1H NMR (DMSO-d6) delta 11.13 (s, 1H, NH), 8.01 (d, J = 8.3 Hz, 1H, Ar-H), 7.48 (d, J = 8.4 Hz, 1H, Ar-H), 6.81 (s, 1H, NH), 3.60 (s, 4H, OCH2*2), 3.29 (d, J = 5.2 Hz, 2H, CH2), 2.41 (s, 6H, NCH2*3). MS (ESI, m/z): Calcd for [M+H]+ C13H17BrN5O2S: 386, 388, found 386, 388.

Molecular Weight:230.09
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:228.93093
Monoisotopic Mass:228.93093
Topological Polar Surface Area:80
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes