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CAS No. : | 88497-27-2 | MDL No. : | MFCD01646092 |
Formula : | C4H4BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FXTDHDQFLZNYKW-UHFFFAOYSA-N |
M.W : | 174.00 | Pubchem ID : | 2794779 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 34.14 |
TPSA : | 51.8 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) : | -7.07 cm/s |
Log Po/w (iLOGP) : | 1.27 |
Log Po/w (XLOGP3) : | 0.41 |
Log Po/w (WLOGP) : | 0.83 |
Log Po/w (MLOGP) : | 0.55 |
Log Po/w (SILICOS-IT) : | 1.02 |
Consensus Log Po/w : | 0.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.73 |
Solubility : | 3.22 mg/ml ; 0.0185 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.06 |
Solubility : | 15.0 mg/ml ; 0.0862 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.14 |
Solubility : | 1.25 mg/ml ; 0.00721 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.02 |
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 |
---|---|---|
75% | With ammonium hydroxide In water at 100℃; Inert atmosphere; Autoclave | A solution of 250 g (1 .05 mol) 3,6-dibromopyridazine in 1 .2 L 25percent aqueous ammonia was heated to 100°C at 11.7 bar overnight in an autoclave. After cooling, the precipitate was filtered off, washed with water and dried to give 137 g (75percent) of the title compound. 1 H-NMR (DMSO-d6): δ= 6.58 (1 H), 6.69 (2H), 7.41 (1 H) ppm. |
75% | With ammonia In water at 100℃; Autoclave | A solution of 250 g (1.05 mol) 3,6-dibromopyridazine in 1.2 L 25percent aqueous ammonia was heated to 100°C at 11.7 bar overnight in an autoclave. After cooling, the precipitate was filtered off, washed with water and dried to give 137 g (75percent) of the title compound. 1 H-NMR (DMSO-d6): δ= 6.58 (1 H), 6.69 (2H), 7.41 (1 H) ppm. |
75% | With ammonia In water at 100℃; Inert atmosphere; Autoclave | Intermediate Example 26h 6-bromo ridazin-3-amine A solution of 250 g (1.05 mol) 3,6-dibromopyridazine in 1.2 L 25percent aqueous ammonia was heated to 100° C at 11.7 bar overnight in an autoclave. After cooling, the precipitate was filtered off, washed with water and dried to give 137 g (75percent) of the title compound. 1 H-NMR (DMSO-d6): δ= 6.58 (1 H), 6.69 (2H), 7.41 (1 H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With bromine; sodium hydrogencarbonate In methanol at 20℃; Inert atmosphere | To a mixture comprising 285 g (1638 mmol) 6-bromopyridazin-3-amine which was prepared according to intermediate example 30h,275 g (3276 mmol) NaHCCb and 2815 mL MeOH was dropwise added 85 mL (1638 mmol) bromine at rt and it was stirred at rt overnight. After further addition of 34 mL (655 mmol) bromine and 55 g (655 mmol) NaHC03,the mixture was stirred overnight again. The solvent was reduced to about 1000 mL and the mixture was poured on 5 L of water. The precipitate was filtered off, washed with water and dried give 41 1 g (99percent) of the title compound. 1 H-NMR (CDCla): δ= 6.14 (1 H), 9.92 (2H) ppm. |
99% | With bromine; sodium hydrogencarbonate In methanol at 20℃; | To a mixture comprising 285 g (1638 mmol) 6-bromopyridazin-3-amine which was prepared according to intermediate example 1 h,275 g (3276 mmol) NaHC03 and 2815 mL MeOH was dropwise added 85 mL (1638 mmol) bromine at rt and it was stirred at rt overnight. After further addition of 34 mL (655 mmol) bromine and 55 g (655 mmol) NaHC03,the mixture was stirred overnight again. The solvent was reduced to about 1000 mL and the mixture was poured on 5 L of water. The precipitate was filtered off, washed with water and dried give 411 g (99percent) of the title compound. 1 H-NMR (CDCls): δ= 6.14 (1 H), 9.92 (2H) ppm. |
99% | With bromine; sodium hydrogencarbonate In methanol at 20℃; Inert atmosphere | Intermediate Example 26 6,8-dibromoimidazo[1 ,2-b]pyridazine To a mixture comprising 285 g (1638 mmol) 6-bromopyridazin-3-amine which was prepared according to intermediate example 26h,275 g (3276 mmol) NaHC03 and 2815 mL MeOH was dropwise added 85 mL (1638 mmol) bromine at rt and it was stirred at rt overnight. After further addition of 34 mL (655 mmol) bromine and 55 g (655 mmol) NaHC03,the mixture was stirred overnight again. The solvent was reduced to about 1000 mL and the mixture was poured on 5 L of water. The precipitate was filtered off, washed with water and dried give 411 g (99percent) of the title compound. 1 H-NMR (CDCb): δ= 6.14 (1 H), 9.92 (2H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 80℃; for 16 h; | To a solution of 6-bromopyridazin-3-amine (3.48 g, 20 mmol) in EtOH/H2O (5/1, 180 mL) was added 2-bromo-1,1-diethoxyethane (11.8 g, 60 mmol), followed by p-toluenesulphonic acid (20.6 mg, 0.12 mmol). The mixture was stirred at 80° C. for 16 hours and then concentrated in vacuo. The resulted solid was washed with H2O (4 mL), collected by filtration, and dried in a vacuum oven overnight at 40° C. to give the title compound as a gray solid (3.9 g, 100percent). MS (ESI, pos. ion) m/z: 198.1 [M+H]+; 1H NMR (400 MHz, CDCl3): δ 8.71 (d, J=9.6 Hz, 1H), 8.44 (d, J=1.6 Hz, 1H), 8.33 (d, J=1.9 Hz, 1H), 7.97 (d, J=9.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.63% | at 80℃; for 7 h; | A 3-amino-6-bromopyridazine (34.8 g, 200 mmol), a 40percent aqueous chloroacetaldehyde solution (58.8, 300 mmol) and 200 mL (158 g) of ethanol were added to a 1000 mL one- The mixture in the reaction flask was stirred at 80 ° C for 7 hours. After the reaction was completed, the mixture was neutralized to pH = 8 with saturated NaHCO 3 solution and added with 400 mL of ethyl acetate. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 × 300 mL). The combined organic phase was washed with 200 mL of water and Washed with 200 mL saturated brine, dried over anhydrous Na2SO4, filtered to remove the drying agent, the filtrate was evaporated to remove the solvent to give a tan solid, the tan solid ethyl acetate: n-hexane mixed solution was yellow crystals, yield 79.63 percent. |