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CAS No. : | 766-55-2 | MDL No. : | MFCD07782103 |
Formula : | C6H5N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VTVRXITWWZGKHV-UHFFFAOYSA-N |
M.W : | 119.12 | Pubchem ID : | 136599 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 32.99 |
TPSA : | 30.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.79 cm/s |
Log Po/w (iLOGP) : | 1.35 |
Log Po/w (XLOGP3) : | 0.33 |
Log Po/w (WLOGP) : | 0.73 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 0.58 |
Consensus Log Po/w : | 0.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.53 |
Solubility : | 3.54 mg/ml ; 0.0298 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.53 |
Solubility : | 35.3 mg/ml ; 0.297 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.66 |
Solubility : | 2.59 mg/ml ; 0.0218 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With palladium on activated charcoal; hydrogen; triethylamine In tetrahydrofuran; methanol for 16 h; | To a stirred solution of 6-chloroimidazo[1,2-bjpyridazine (800 mg, 5.21 mmol) in methanol (20 mL) and tetrahydrofuran (20 mL) was added triethylamine (0.8 mL, 5.74mmol) followed by Pd/C (100 mg, 0.094 mmol). The mixture was stirred under hydrogen atmosphere for 16h. The reaction mixture was filtered through celite and the celite bed was washed with methanol. The combined filtrate was concentrated then suspended in water and extracted with ethyl acetate (3x). The organic layer was dried over Na2SO4 and filtered to give the imidazo[1,2-bjpyridazine (550 mg, 87percent) as off white solid. LCMS[m/z 120 (M+H)j; ‘H NMR (300 MHz, DMSO-d6) ö 8.51 (dd, J4.53, 1.51 Hz, 1H) 8.29(d,J0.76Hz, 1 H) 8.05-8.19(m, 1 H)7.79(d,J1.13 Hz, 1 H) 7.22 (dd,J=9.44,4.53 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 2 h; Reflux | The imidazo [1,2-b] pyridazine (6.0g, 50 . 4mmol), NBS (6.0g, 75 . 6mmol) and a catalytic amount of AIBN is added to the 50 ml chloroform, heating to reflux the reaction 2 hours, TLC detection of the reaction process, the raw materials of the reaction after cooling to room temperature stirring under the conditions of the ice bath, a precipitate out, filtered and the filtrate concentrated to get the pure product.The pure product as a pale yellow solid, yield: 75percent |
75% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 2 h; Reflux | The imidazo [1,2-b] pyridazine (6.0 g, 50.4 mmol), NBS (6.0 g, 75.6 mmol) and a catalytic amount of AIBN were added to 50 mL of chloroform and the reaction was heated to reflux for 2 hours, The reaction solution was cooled to room temperature when the raw material disappeared with the TLC detection of the reaction process, and a precipitate precipitated after the solution stirred in an ice bath. After filtering, the filtrate concentrated under reduced pressure to give the pure product. A pale yellow solid, yield: 75percent. 1H NMR (CDCl3, 400 MHz, δ ppm): 8.50 (d, J = 3.6 Hz, 1H), 8.01-7.98 (m, 1H), 7.84 (s, 1H), 7.15-7.12 (m, 1H). ESI-MS m/z : 200.1 [M+H]+. |
74% | With N-Bromosuccinimide In chloroform for 0.5 h; Reflux | Example 15 -4 Synthesis of 3-bromo-imidazo[1,2-b]pyridazine To imidazo[1,2-b]pyridazine 1*b (10 g) stirring in chloroform (250 ml) was added N-bromosuccinimide (15.7 g) at 5 °C. The cooling bath was removed and the reaction was heated to reflux which was maintained for 30 minutes. After leaving to cool overnight the reaction mixture was concentrated under reduced pressure. The residue was redissolved in ethyl acetate (500 ml), washed with potassium carbonate solution (3 x 200 ml) then brine (100 ml). The organic extract was dried with magnesium sulphate and concentrated in vacuo to give 3-bromo-imidazo[1,2-b]pyridazine 2*b, 12.3 g (74percent). 1H-NMR (400MHz, DMSO-D6) : δ = 8.68 (1 H, d, 4.4 Hz, ArH), 8.20 (1 H, d, 9.2 Hz, ArH), 7.95 (1 H, s, ArH), 7.33 (1 H, q, 3.4 Hz, ArH). |
36% | at 0 - 20℃; for 1 h; | To a stirred solution of imidazo[1,2-bjpyridazine (200 mg, 1.679 mmol) in acetic acid (10 mL) was added bromine (0.2 mL, 3.88 mmol) at 0 °C. The reaction mixture was allowed to warm to room temperature and stir for 1 hr. The reaction mixture was neutralized with iN sodium hydroxide, poured into EtOAc (20 mL) and 10percent NaHCO3 solution. The layers were separated and the aqueous layer extracted with EtOAC (3x20ml). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give 3-bromoimidazo[1,2-bjpyridazine (120 mg, 36percent) as light brown solid. ‘H NMR (400 MHz, DMSO-d6) ö 8.68 (dd, J=4.52, 1.51 Hz, 1 H) 8.19 (dd, J=9.54, 1.51 Hz, 1 H) 7.94 (s, 1 H) 7.28-7.39 (m, 1 H). |
9.9 g | With N-Bromosuccinimide In chloroform for 0.5 h; Reflux | theImidazo [1,2-b] pyridazin(50mmol) dissolved in Chloroform (50 ml), Bromosuccinimide(55 mmoles) was slowly added into the reaction . at reflux System was stirredfor 30 minutes. After cooling to room temperature, the pH was adjusted to 8-9 usingsaturated aqueous sodium carbonatesolution and extracted with ethyl acetate. The extract was washed with water andsaturated brine. After dried overanhydrous sodium sulfate and concentrated to give 9.9 g of the title compound. |
9.9 g | With N-Bromosuccinimide In chloroform for 0.5 h; Reflux | The imidazo [l, 2_b] pyridazine ¢ .0 g, 50 mmol) was dissolved in chloroform (50 ml), N- bromobutyrate ni imide (NBS) (9.8 g, 55 mmol mol) was slowly added thereto.Was refluxed for 30 minutes.After cooling to room temperature, the PH value was adjusted to 8-9 with saturated sodium carbonate solution, extracted with ethyl acetate.The extract was washed with water, brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound 9.9 g. |
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