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CAS No. : | 1161847-32-0 | MDL No. : | MFCD24642467 |
Formula : | C7H8ClN3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MNDSXVIOHQUROW-UHFFFAOYSA-N |
M.W : | 201.61 | Pubchem ID : | 57786714 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.53 |
TPSA : | 78.1 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.66 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 1.23 |
Log Po/w (WLOGP) : | 0.9 |
Log Po/w (MLOGP) : | 0.73 |
Log Po/w (SILICOS-IT) : | 0.99 |
Consensus Log Po/w : | 1.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.01 |
Solubility : | 1.98 mg/ml ; 0.00981 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.47 |
Solubility : | 0.687 mg/ml ; 0.00341 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.4 |
Solubility : | 0.81 mg/ml ; 0.00402 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.2 |
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 |
---|---|---|
100% | In water; isopropyl alcohol; at 80.0℃; for 4.0h; | Example 9.; A mixture of crude 3-amino-6-chloro-pyridazine-4-carboxylic acid ethyl ester (3.93 g, "19.5 mmol"), 90 mL of isopropanol, and 20 mL of a 50% chloroacetaldehyde solution was stirred at 80 0C for 4 h, then concentrated to remove isopropanol. The resulting orange liquid was partitioned between 100 mL of ether and 100 mL of a saturated aq. NaHCOs solution. The organic layer was sequentially washed with 100 mL of water and 100 mL of a saturated aq. NaCl solution, dried over MgSO4, filtered and concentrated to 5.00 g (113% crude) of 6-chloro-imidazo[l,2-b]pyridazine-8-carboxylic acid ethyl ester as an orange liquid that was used without further purification. |
67% | In water; isopropyl alcohol; at 80.0℃; for 4.0h; | Chloroacetaldehyde (50% in H2O) (5.04 mL, 39.7 mmol) was added to ethyl 3-amino-6- chloropyridazine-4-carboxylate (1.00 g, 4.96 mmol) in isopropanol (20 mL). The solution was heated at 80 C for 4 h. The reaction mixture was concentrated and the resulting orange liquid was partitioned between ether (30 mL) and saturated aq. NaHCOs solution (20 mL). The organic layer was washed with water (20 mL) and saturated aq. NaCl solution (20 mL), dried over MgSCn, filtered, and concentrated. The residue was purified by column chromatography on silica gel (60%? 80% ethyl acetate in hexanes; 25 g column) to afford ethyl 6-chloroimidazo[l,2-Z>]pyridazine-8-carboxylate (750 mg, 3.32 mmol, 67% yield) as a green solid: NMR (400MHz, METHANOLS) d 8.23 (d, J=1.5 Hz, 1H), 7.88 (d, J=1.3 Hz, 1H), 7.73 (s, 1H), 4.52 (q, J=7.0 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H); LCMS (ESI) mle 226.0 [(M+H) + , calcd for C9H9N3O2CI 226.0]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With ammonia; triethylamine; In 1,4-dioxane; at 100℃; for 48h; | Example 8.; A sealed tube was charged with <strong>[34127-22-5]3,6-dichloro-pyridazine-4-carboxylic acid ethyl ester</strong> (4.37 g, 19.8 mmol), 80 mL of dioxane and triethylamine (5.6 mL, 40 mmol). Ammonia was rapidly bubbled in via a dipersion tube for 2 minutes. The tube was capped and the yellow solution was stirred at 100 0C for 2 d, then allowed to cool. The mixture was transferred to a flask, using diethyl ether in rinsings, and concentrated to a yellow solid. The solid was partitioned between 100 mL of water and 100 mL of ethyl acetate. The aqueous layer was extracted with two 100 mL portions of ethyl acetate. There initially is undissolved solid in the aqueous layer that eventually disappears with the ethyl acetate extractions. The combined organic layers were concentrated to 3.93 g (99% crude) of 3- amino-6-chloro-pyridazine-4-carboxylic acid ethyl ester as a yellow solid that was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In N,N-dimethyl-formamide; at 60.0℃; for 4.0h; | Ethyl 3-amino-6-chloropyridazine-4-carboxylate (600 mg, 2.98 mmol) was added to 2- bromo-l-phenylethanone (711 mg, 3.57 mmol) in DMF (10 mL). The solution was heated at 60 C for 4 h. The reaction mixture was partitioned between ether (30 mL) and saturated aq. NaHCCb solution (20 mL). The organic layer was washed with water (20 mL) and saturated aq. NaCl solution (20 mL), dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography on silica gel (5? 20% ethyl acetate in hexanes; 40 g column) to afford ethyl 6-chloro-2-phenylimidazo[l,2- Z>]pyridazine-8-carboxylate (600 mg, 1.989 mmol, 67% yield) as a yellow solid: NMR (400MHz, DMSO-de) delta 9.08 (s, 1H), 8.12 - 8.08 (m, 2H), 7.74 (s, 1H), 7.55 - 7.49 (m, (0233) 2H), 7.45 - 7.40 (m, 1H), 4.49 (q, J=7.2 Hz, 2H), 1.42 (t, J=7.0 Hz, 3H); LCMS (ESI) mle 302.0 [(M+H)+, calcd for C15H13N3O2CI 302.1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In N,N-dimethyl-formamide; at 60.0℃; for 16.0h; | Ethyl 3-amino-6-chloropyridazine-4-carboxylate (200 mg, 0.992 mmol) was added to 2- bromo-l-(2-methoxyphenyl)ethanone (227 mg, 0.992 mmol) in DMF (3 mL). The solution was heated to 60 C for 4 h. Additional 2-bromo-l-(2-methoxyphenyl)ethanone (227 mg, 0.992 mmol) was added and the reaction was heated to 60 C for 12 h. The reaction mixture was partitioned between ether (30 mL) and saturated aq. NaHCC solution (20 mL). The organic layer was washed with water (20 mL) and saturated aq. NaCl solution (20 mL), dried over MgSO, filtered and concentrated. The residue was purified by column chromatography on silica gel (5? 20% ethyl acetate in hexanes; 25 g column) to afford ethyl 6-chloro-2-(2-methoxyphenyl)imidazo[l,2-)]pyridazine-8- carboxylate (200 mg, 0.603 mmol, 61 % yield) as a yellow solid: NMR (400MHz, DMSO-de) delta 8.78 (s, IH), 8.34 (dd, J=7.8, 1.8 Hz, IH), 7.73 (s, IH), 7.45 - 7.39 (m, IH), 7.19 (d, J=7.8 Hz, IH), 7.13 (td, J=7.5, 1.0 Hz, IH), 4.49 (q, J=7.0 Hz, 2H), 4.01 (s, 3H), 1.42 (t, J=7.2 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | In N,N-dimethyl-formamide; at 60.0℃; for 4.0h; | Ethyl 3-amino-6-chloropyridazine-4-carboxylate (270 mg, 1.339 mmol) was added to 2- bromo-l-(4-(trifluoromethyl)phenyl)ethanone (358 mg, 1.339 mmol) in DMF (6 mL). The solution was heated at 60 C for 4 h. The resulting orange liquid was partitioned between ether (30 mL) and saturated aq. NaHCC solution (20 mL). The organic layer was washed with water (20 mL) and saturated aq. NaCl solution (20 mL), dried over MgS04, filtered and concentrated. The residue was purified by column chromatography on silica gel (5? 20% ethyl acetate in hexanes; 40 g column) to afford ethyl 6-chloro-2-(4-(trifluoromethyl)phenyl)imidazo[l,2-)]pyridazine-8-carboxylate (190 mg, 0.514 mmol, 38% yield) as a yellow solid: NMR (400MHz, DMSO-de) delta 9.23 (s, IH), 8.31 (d, J=8.0 Hz, 2H), 7.89 (d, J=8.0 Hz, 2H), 7.79 (s, IH), 4.49 (q, J=7.1Hz, 2H), 1.42 (t, J=7.2 Hz, 3H); LCMS (ESI) m/e 370.0 [(M+H) + , calcd for C16H12N3O2F3CI 370.1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | In ethanol; at 80.0℃; for 28.0h; | Ethyl 3-amino-6-chloropyridazine-4-carboxylate (300 mg, 1.488 mmol) was added to 2- bromo-l-(pyridin-3-yl)ethanone (357 mg, 1.786 mmol) in Ethanol (10 mL). The solution was heated to 80 C for 4 h. Additional 2-bromo-l-(pyridin-3-yl)ethanone (200 mg, 1 mmol, 06 eq) was added and the reaction was heated to 80 C for 12 h. LCMS showed 50% conversion of starting material to the desired product. Additional 2-bromo-l-(pyridin-3-yl)ethanone (200 mg, 1 mmol, 06 eq) was added and the reaction was heated to 80 C for 12 h. The reaction mixture was concentrated to remove ethanol. The resulting orange liquid was partitioned between ether (30 mL) and saturated aq. NaHCC solution (20 mL). The organic layer was washed with water (20 mL) and saturated aq. NaCl solution (20 mL), dried over MgS04, filtered and concentrated. The residue was purified by column chromatography on silica gel (50? 80% ethyl aceatee in hexane ethyl acetate in hexanes; 40 g column) to afford ethyl 6-chloro-2-(pyridin-3-yl)imidazo[l,2- Z>]pyridazine-8-carboxylate (70 mg, 0.231 mmol, 16% yield) as a red oil: NMR (400MHz, CHLOROFORM-d) delta 9.20 (d, J=1.8 Hz, 1H), 8.61 (dd, J=4.8, 1.5 Hz, 1H), 8.38 - 8.32 (m, 2H), 7.62 (s, 1H), 7.44 - 7.36 (m, 1H), 4.56 (q, J=7.0 Hz, 2H), 1.50 (t, J=7.2 Hz, 3H); LCMS (ESI) mle 303.1 [(M+H) + , calcd for C14H12N4O2CI 303.1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With trifluoroacetic acid; for 3.0h;Reflux; | A mixture of ethyl 6-chloro-3-((4-methoxybenzyl)amino)pyridazine-4-carboxylate (1.2 g, 3.73 mmol) and TFA (5.75 ml, 74.6 mmol) was heated at reflux for 3 h. The reaction mixture was concentrated and transferred to a separatory funnel containing saturated aqueous NaHCC solution (15 mL). The aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine (15 mL), dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography on silica gel (60%? 80% ethyl acetate in hexanes; 12 g column) to afford ethyl 3- amino-6-chloropyridazine-4-carboxylate (700 mg, 3.47 mmol, 93% yield) as a green solid: NMR (400MHz, CHLOROFORM-d) delta 7.77 (s, 1H), 7.00 (s br, 2H), 4.40 (q, J=7.0 Hz, 2H), 1.40 (t, J=7.2 Hz, 3H); LCMS (ESI) m/e 202.0 [(M+H)+, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h; | To <strong>[1161847-32-0]ethyl 3-amino-6-chloropyridazine-4-carboxylate</strong> (4.0 g, 19.9 mmol) in dry THF (1 niL) was slowly added LiAlH4 (2.42 g, 64 mmol) at 0 C. The mixture was stirred at 0 C for 30 min. Excess reagent was quenched carefully with water (1 mL), then 15% aqueous NaOH (1 mL) was added. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield (3-amino-6-chloropyridazin-4- yl) methanol (1.0 g, 32%). MS m/z 160.1, 162.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | at 100.0℃; for 48.0h; | A mixture of ethyl 3-amino-6-chloro-pyridazine-4-carboxylate (360 mg, 1.8 mmol, 1.0 eq.) and chloroacetone (3.0 mL) was stirred at 100 C for 48 h, then cooled, diluted with ether and filtered. The solid was dissolved in methanol and purified with a C18 column to give 6-chloro-2- methyl-imidazo[1,2-b]pyridazine-8-carboxylic acid (150 mg, 40%). 1H NMR (methanol-d4) d: 8.36 (br s, 1H), 8.24 (d, J= 7.6 Hz, 1H), 2.64 (s, 3H). |
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