4-PYRIDIN-2-YL-THIAZOL-2-YLAMINE

(0.01 mol) of' -bromo 2-pyridineethanone, 0.76 g (0.01 mol) of thiourea and 50 mL of ethanol were added to a 100 mL round bottom flask and refluxed for 4 h.After completion of the reaction, the ethanol solvent was distilled off under reduced pressure.Column chromatography was performed on DCM: MeOH: NHTo a solution of 2 (11.2 mmol) in 25 ml of ethanol at room temperature was added thioureaGeneral procedure T. 4-Pyridin~3-yl-thiazol-2-ylamine To a solution of 2-bromo-l-pyridin-2-yl-ethanone (leqv, 10 g, 50.0 mmol) in ethanol (100 ml) was added thiourea (1.02eqv, 3.88 g, 51.0 mmol) and the reaction mixture heated to 90A solution of thiourea (1.2 g, 15 mmol) in H2-bromo-1-(pyridin-2-yl)ethanone hydrobromide (500 mg, 1.78 mmol) and thiourea (542 mg, 7.12 mmole, 4 eq) were stirred in ethanol at 90 °C for 3 hours and then cooled and concentrated. The residue was partitioned between ethyl acetate and saturated NaHCCb. The organic phase was washed with water and brine, and then concentrated. The light yellow solid obtained was triturated with methylene chloride and dried (280 mg, 89percent). NMR (300 MHz, CDCh): δ 8.59 (d, J= 4.4 Hz, 1H), 7.89 (d, J= 7.9 Hz, 1H), 7.72 (td, J= 7.9, 1.8 Hz, 1H), 7.31 (s, 1H), 7.22-6.94 (m, 1H); Calculated for C8H7N3S, To 2-bromo-1-pyridin-2-yl-ethanone (1 g, 5mmol) in ethanol was added thiourea (340 mg, 5.1 mmol). The mixture was stirred at 70°C.The reaction was monitored via LC/MS. After 2 h, the reaction mixture was cooled to roomtemperature and precipitate was formed. The precipitate was collected by vacuum filtrationand washed with acetone. The solid was dissolved in 2MNaOH (25 mL) and extracted withEtOAc (3 x 50 mL). The combined organic layers were dried over Na2SO4 and concentrated invacuo to give 3 (497 mg, 56percent yield), as an off-white solid. 1H NMR: (300 MHz, CD3OD): δ7.24–7.31 (m, 2H), 7.80–7.92 (m, 2H), 8.49–8.51 (m, 1H); 13C NMR: (300 MHz, CD3OD): δ105.9, 120.8, 122.3, 137.3, 148.5, 149.5, 152.4; HRMS MS ESI m/z calcd for C8H7N3S (M+H)+178.0433, found 178.0441 (Δ 0.8 ppm). All data are consistent with literature values [19].

Molecular Weight:177.23
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:177.03606841
Monoisotopic Mass:177.03606841
Topological Polar Surface Area:80
Heavy Atom Count:12
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes