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CAS No. : | 64068-00-4 | MDL No. : | MFCD19203440 |
Formula : | C5H6ClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HSAHCMOZFNSMLH-UHFFFAOYSA-N |
M.W : | 143.57 | Pubchem ID : | 12353664 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.41 |
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) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 1.39 |
Log Po/w (XLOGP3) : | 0.82 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 0.74 |
Log Po/w (SILICOS-IT) : | 1.31 |
Consensus Log Po/w : | 1.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.74 |
Solubility : | 2.61 mg/ml ; 0.0182 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.49 |
Solubility : | 4.65 mg/ml ; 0.0324 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.27 |
Solubility : | 0.766 mg/ml ; 0.00533 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
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 |
---|---|---|
43.5% | With ammonia In ethanol at 120℃; for 12 h; Heating in a sealed tube | [Linholter, S., et a/, Acta Chem. Scand. 15: 1660-1666 (1961 )]. To a solution of 3,6-dichloro-4-methyl-pyridazine (200 mg) in ethanol (3ml) was added liquid ammonia (3 ml). The reaction mixture was heated at 120 0C in a sealed tube for 12 h. After cooling to room temperature, methanol and ammonia were evaporated. The residue was purified by flash chromatography (ethyl acetate) to afford 153 mg of mixture of 7 and 10 (1 :1 ), (87percent), which was used without any further separation. |
10% | at 120℃; for 18 h; Autoclave | A mixture of 3,6-dichloro-4-methylpyridazine (5 g, 30.7 mmol) and concentrated NH40H solution (100 ml) was heated to 120° in a sealed autoclave for 18 hrs at 6 bar. The mixture was cooled to r.t, diluted with water (200 ml) and stirred in an ice bath for 2 hrs. The solid was collected by filtration, washed with water and dried. The filtrate was extracted with CH2Cl2/MeOH (9: 1). The organic was washed with brine, dried over MgSC^, filtered and evaporated. The precipitate from the reaction mixture and the solid isolated by extraction were combined. This crude product was purified by column chromatography using a CH2Cl2/MeOH gradient as eluent, to provide 6-chloro-4-methylpyridazin-3-amine (456 mg, 10percent) and 6-chloro-5-methylpyridazin- 3-amine (350 mg, 8percent>), both as off-white solids. MS: M = 144.1 (M+H)+ (both isomers) |
22.4 g | at 110℃; for 48 h; Sealed tube | In a sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25percent, 300 mL). The reaction mixture was heated at 110 °C for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2C12, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step. |
22.4 g | at 110℃; for 48 h; | In a sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25percent, 300 mL). The reaction mixture was heated at 110 °C for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2C12, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43.5% | With ammonia In ethanol at 120℃; for 12 h; Heating in a sealed tube | [Linholter, S., et a/, Acta Chem. Scand. 15: 1660-1666 (1961 )]. To a solution of 3,6-dichloro-4-methyl-pyridazine (200 mg) in ethanol (3ml) was added liquid ammonia (3 ml). The reaction mixture was heated at 120 0C in a sealed tube for 12 h. After cooling to room temperature, methanol and ammonia were evaporated. The residue was purified by flash chromatography (ethyl acetate) to afford 153 mg of mixture of 7 and 10 (1 :1 ), (87percent), which was used without any further separation. |
10% | at 120℃; for 18 h; Autoclave | A mixture of 3,6-dichloro-4-methylpyridazine (5 g, 30.7 mmol) and concentrated NH40H solution (100 ml) was heated to 120° in a sealed autoclave for 18 hrs at 6 bar. The mixture was cooled to r.t, diluted with water (200 ml) and stirred in an ice bath for 2 hrs. The solid was collected by filtration, washed with water and dried. The filtrate was extracted with CH2Cl2/MeOH (9: 1). The organic was washed with brine, dried over MgSC^, filtered and evaporated. The precipitate from the reaction mixture and the solid isolated by extraction were combined. This crude product was purified by column chromatography using a CH2Cl2/MeOH gradient as eluent, to provide 6-chloro-4-methylpyridazin-3-amine (456 mg, 10percent) and 6-chloro-5-methylpyridazin- 3-amine (350 mg, 8percent>), both as off-white solids. MS: M = 144.1 (M+H)+ (both isomers) |
22.4 g | at 110℃; for 48 h; Sealed tube | In a sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25percent, 300 mL). The reaction mixture was heated at 110 °C for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2C12, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step. |
22.4 g | at 110℃; for 48 h; | In a sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25percent, 300 mL). The reaction mixture was heated at 110 °C for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2C12, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; | 6-Chloro-4-methylpyridazin-3-amineA 100 mL flask was charged with 4-bromo-6-chloropyridazin-3-amine (1 g, 4.80 mmol), dimethylzinc (9.59 mL, 9.59 mmol), Pd(PPh3)4 (0.277 g, 0.240 mmol) and DMF (10 mL). The reaction mixture was stirred at RT. Then the reaction mixture was quenched with MeOH and concentrated. The crude product was loaded onto a 10 g SCX SPE, and 3 volumes of MeOH followed by 3 volumes of 2N ammonia in MeOH were added. The fractions were combined and concentrated to afford 6-chloro-4-methylpyridazin-3-amine (693 mg, 80percent yield). |
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