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CAS No. : | 2164-61-6 | MDL No. : | MFCD01646333 |
Formula : | C5H4N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RUUOPSRRIKJHNH-UHFFFAOYSA-N |
M.W : | 124.10 | Pubchem ID : | 269369 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 28.99 |
TPSA : | 63.08 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) : | -7.11 cm/s |
Log Po/w (iLOGP) : | 0.55 |
Log Po/w (XLOGP3) : | -0.08 |
Log Po/w (WLOGP) : | 0.17 |
Log Po/w (MLOGP) : | -0.44 |
Log Po/w (SILICOS-IT) : | 0.32 |
Consensus Log Po/w : | 0.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.99 |
Solubility : | 12.8 mg/ml ; 0.103 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.79 |
Solubility : | 20.0 mg/ml ; 0.161 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.98 |
Solubility : | 12.9 mg/ml ; 0.104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.31 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
3.3 mg of <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong>, 15 mg of 1-hydroxybenzotriazole and 15 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydride were added in order to an N-methylpyrrolidone (0.3 ml) solution of 15 mg of 4-(2-cyano-phenoxy)-5-(4-methanesulfonyl-phenoxy)-benzene-1,2-diamine obtained in Example 17, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, and washed with saturated sodium bicarbonate solution, and the solvent was evaporated away under reduced pressure. The resulting residue was dissolved in 0.2 ml of N-methylpyrrolidone, and 5 mg of ytterbium trifluoromethanesulfonate was added to it, and the reaction liquid was stirred overnight at 140C. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1 % trifluoroacetic acid]. The solvent of the resulting fraction was evaporated away under reduced pressure to obtain the entitled compound as a brown solid. 1H-NMR(CD3OD)delta: 3.10(3H,s), 6.92(1H,d,J=7.6Hz), 6.99(2H,d,J=8.6Hz), 7.20(1H,t,J=7.6Hz), 7.58(1H,t,J=7.6Hz), 7.64(1H,d,J=7.6Hz), 7.70-7.80(2H,m), 7.87(2H,d,J=8.6Hz), 7.96-8.02(1H,m), 8.58(1H,brs), 9.36(1H,brs) ESI-MS(m/e):484[M+H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
DIPEA (1.92 ml.) was added to a suspension of <strong>[2164-61-6]3-pyridazinecarboxylic acid</strong> (500 mg) and HATU (1.53 g) in DMF (10 ml.) at room temperature under nitrogen. After 10 min [4-(4, 4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]amine (802 mg) was added and the reaction was heated to 5O0C for 4 h. The reaction was cooled evaporated in vacuo and partitioned between DCM (20 ml.) and sodium bicarbonate solution (10 ml_). The DCM was washed with sodium bicarbonate, dried by passing through a hydrophobic frit and evaporated in vacuo. The crude material was purified using a 120 g silica ISCO cartridge eluting with a gradient of 0-100% EtOAc in cyclohexane to give the title compound. MS calcd for (C17H20BN3O3 + H)+ : 326 MS found (electrospray) : (M+H)+ = 326 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Pyridazinecarboxylic acid (48 mg) was dissolved in a solution of DMF (3 ml_), DIPEA (182 mul_) and HATU (201 mg), the reaction was stirred at room temperature for 15 mins. Intermediate 64 (150 mg) in DMF (1 ml.) was added and the mixture was stirred at 5O0C under nitrogen for 22 h. The reaction mixture was evaporated in vacuo and was partitioned between DCM and saturated sodium bicarbonate solution. The organic phase was collected and dried by passing through a hydrophobic frit and evaporated in vacuo. The crude material was purified using a 12 g silica ISCO cartridge eluting with a gradient of 5 - 100% EtOAc in cyclohexane to give the title compound. MS calcd for (C29H32N4O4S + H)+ : 533 MS found (electrospray) : (M+H)+ = 533 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of <strong>[2164-61-6]3-pyridazinecarboxylic acid</strong> (66 mg), HATU (220 mg) and DIPEA (248 mg) were dissolved in DMF (5 ml.) and the reaction was stirred at room temperature for 1 h. Methyl 5- (4-aminophenyl)-3-[[(frans-4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-2- thiophenecarboxylate (200 mg, a synthesis of which is described as Intermediate 9) was added and the reaction was stirred at room temperature for 18 h, then at 5O0C over a weekend. HATU (220 mg), DIPEA (248 mg) and <strong>[2164-61-6]3-pyridazinecarboxylic acid</strong> (66 mg) were added and the reaction was stirred at 5O0C for 4 h. The reaction was evaporated in vacuo and partitioned between DCM and sodium bicarbonate solution. The organic phases were separated, dried using a hydrophobic frit and evaporated in vacuo. The crude material was purified by ISCO Companion silica chromatography, eluting with a gradient 5-100% EtOAc in cyclohexane to give the title compound. MS calcd for (C28H32N4O4S + H)+: 521 MS found (electrospray): (M+H)+ = 521 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With O-(benzotriazol-1-yl )-N,N,N' ,N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; | g) (S)-N-(5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-3-yl)pyridazine-3-carboxamide <strong>[2164-61-6]Pyridazine-3-carboxylic acid</strong> (CAN 2164-61-6; 43.1 mg, 347 mumol) was suspended in DMF (1.0 mL). TBTU (112 mg, 347 mumol), ethyldiisopropylamine (102 mg, 131 mul, 789 mumol,) and 5-(4-chloro-phenyl)-6-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridin-3-ylamine (0.100 g, 316 mumol) were added and the reaction mixture was stirred at room temperature for 1 h. The rection mixture was extracted with ethyl acetate and 1M citric acid solution; the organic phase was dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, 10% to 50% ethyl acetate in heptane) to give 0.11 g (83%) of the title compound as white solid; MS (EI) 423.1 (M+H)+. |
83% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; | g) (S)-N-(5-(4-chlorophenyl)-6-(l,l, l-trifluoropropan-2-yloxy)pyridin-3-yl)pyridazine-3- carboxamide<strong>[2164-61-6]Pyridazine-3-carboxylic acid</strong> (CAN 2164-61-6; 43.1 mg, 347 muiotaetaomicron) was suspended in DMF (1.0 mL) . TBTU (112 mg, 347 muiotaetaomicron), ethyldiisopropylamine (102 mg, 131 mu, 789 muiotaetaomicron,) and 5-(4-chloro-phenyl)-6-((S)-2,2,2-trifluoro-l-methyl-ethoxy)-pyridin-3-ylamine (0.100 g, 316 muiotaetaomicron) were added and the reaction mixture was stirred at room temperature for 1 h. The rection mixture was extracted with ethyl acetate and 1M citric acid solution; the organic phase was dried with MgS04 and concentrated in vacuo. The crude material was purified by flashchromatography (silica gel, lOg, 10% to 50% ethyl acetate in heptane) to give 0.11 g (83%) of the title compound as white solid; MS (EI) 423.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; HATU; In N,N-dimethyl-formamide; at 23℃; for 16h; | Pyridazin-3-yl(7-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanoneTo a suspension of 7-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (50 mgs, 0.16 mmol), <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (30 mgs, 0.24 mmol), HATU (91 mgs, 0.24 mmol), in DMF (1.0 mL) was added NMM (0.05 mL, 0.48 mmol) and the resulting solution was stirred at 23 C. for 16 h. The reaction mixture was then diluted with water/acetonitrile (10:1) and the solid formed was then washed with water, diethylether and dried to give the title compound. MS found for C21H16F3N3O as (M+H)+ 384.1 1H NMR (400 MHz, dmso-d6): mixture of rotomers (1.5:1): major rotomer: delta 8.93 (m, 2H), 7.96-7.91 (m, 3H); 7.91-7.55 (m, 6H); 7.32 (m, 1H); 4.90 (s, 2H); 3.44-3.41 (m, 2H); 2.86-2.848 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Step A: N-((1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)pyridazine-3-carboxamide <strong>[2164-61-6]Pyridazine-3-carboxylic acid</strong> (0.122 g, 0.979 mmol, Matrix) was dissolved in DMF (3 mL). HATU (0.447 g, 1.17 mmol) was added and the mixture stirred at ambient temperature for about 1 min. TEA (0.6 mL, 4.30 mmol) and (1S,3S,4R)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentylamine (0.250 g, 0.98 mmol, Example No.1, Step D) were added and the resulting mixture was stirred at ambient temperature for about 1 h. The mixture was diluted with DCM (10 mL) and washed with saturated aqueous NaHCO3 (5 mL). The organic layer was collected, dried over MeSO4, filtered and evaporated. The resulting solid was sequentially triturated with Et2O and MeOH, filtered and the resulting solid dried to give N-((1S,3S,4S)-3-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-4-methylcyclopentyl)pyridazine-3-carboxamide (0.092 g, 26%); LC/MS (Table 1, Method a) Rt=1.58 min; MS m/z: 362 (M+H)+. Jak3 IC50=C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Compound 18 BTC (1 .15 eq, 0.100 mmol, 30 mg) was dissolved in dry THF (5 ml) under an atmosphere of argon<strong>[2164-61-6]Pyridazine-3-carboxylic acid</strong> (3.5 eq, 0.305 mmol, 33 mg) was added. syn-Collidine (8 eq, 0.700 mmol, 0.092 ml) was slowly added via syringe and the white suspension was stirred at room temperature for 10 min. The amine (1 eq, 0.087 mmol, 70 mg) and DIPEA (10 eq, 0.872 mmol, 0.150 ml) were added via syringe. The reaction mixture was stirred for 12 h at room temperature and quenched by the addition of water. After removing the organic solvent under reduced pressure the aqueous phase was extracted with EtOAc (3 x 50 ml). The organic phase was washed with saturated NaHC03 solution (2 x 50 ml), aqueous HCI solution (5 %, 2 x 50 ml), water (1 x 50 ml) and brine (1 x 50 ml). After drying over Na2S04 and filtration, the solvent was removed under reduced pressure. Column chromatography (CHCI3:MeOH; 1 .5 % MeOH) yielded the product as an orange oil (58 mg, 73 %). The oil (1 eq, 0.058 mmol, 56 mg) and phenylsilane (8 eq, 0.466 mmol, 0.057 ml) were dissolved in dry THF under an atmosphere of argon and exclusion of light. Pd[P(Ph)3]4 (0.5 eq, 0.029 mmol, 34 mg) was added and the mixture was stirred 12 h at room temperature. After adding 3 drops of acetic acid the solvent was removed under reduced pressure. The product was isolated after preparative HPLC purification as a white powder (7 mg, 15 %). H-NMR (DMSO-ds, 400 MHz): delta [ppm] 3.08 (m, 1 H), 3.17 (m, 1 H), 3.77 (s, 3H), 3.91 (s, 3H), 5.00 (m, 1 H), 7.57 (t, J = 9.0 Hz, 1 H), 7.80 (m, 4H), 7.99 (m, 5H), 8.04 (m, 1 H), 8.1 1 (d, J = 8.9 Hz), 8.35 (dd, J = 1 .6 Hz), 9.10 (d, J = 7.0 Hz), 9.49 (dd, Ji = 5.0 Hz, J2 = 1 .5 Hz), 9.71 (s, 1 H), 10.59 (s, 1 H), 1 1 .18 (s, 1 H), 1 1 .34 (s, 1 H), 1 1 .54 (s, 1 H). HR-MS: [M-H]- calculated: 787.2106 [M-H]- found: 787.21 1 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere; | General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.24 g | With triethylamine; In tetrahydrofuran; at 0℃; for 6.5h; | To a mixture of <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (1.07 mL, 12.09 mmol) and TEA (anhydrous, 3.36 mL, 24.17 mmol) in THF (60.4 mL) was added isobutyl chloroformate (1.88 mL, 14.50 mmol) at 0 C. The resulting mixture was stirred at the same temperature for 6.5 h. Next, water (50 mL) was added to the mixture, and the resulting mixture was extracted with CHCl3(70 mL x 4). The combined extracts were dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by CombiFlash on a 125 g silica gel column using 0-100% EtOAc gradient in hexanes as the eluent to give Example 395.3 (1.24 g). LCMS-ESI (pos.): 139.1 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With hydrogenchloride;Reflux; | A mixture of <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (1.00 g, 8.06 mmol), ethanol (18.5 mL) and cone. HC1 (0.370 mL, 12.1 mmol) was refluxed overnight. The reaction mixture was concentrated and diluted with EtOAc. Saurated NaHC03 solution was added and the mixture was extracted with EtOAc (2X). The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to afford the product as a tan solid (671 mg, 55%). LCMS (FA): m/z 153 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 2h; | General procedure: Tetrahydro-2H-pyran-4-carboxylic acid (26.2 mg, 0.202 mmol), EDC hydrochloride (38.7mg, 0.202 mmol), and 1-hydroxybenzotriazole(27.2mg, 0.202 mmol) were added to a solution of 8 (75.0mg,0.168mmol) in DMF (1.50mL) at room temperature. The mixture was stirred at room temperature for 2 h, sat.NaHCO3 aqueous solution was added, and the mixture was extracted with CHCl3. The organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography(CHCl3/MeOH) to give the desired compound as a white solid(77mg, 82%). 1H NMR (DMSO-d6) delta 1.38-1.65 (8H, m), 1.84-1.92 (2H,m), 2.14-2.22 (2H, m), 2.32-2.41 (1H, m), 3.08 (3H, s), 3.26-3.34 (2H,m), 3.56-3.67 (1H, m), 3.82-3.90 (2H, m), 4.01 (3H, s), 4.04 (3H, s),4.89-4.98 (1H, m), 7.29 (1H, s), 7.73 (1H, d, J=7.4Hz), 8.05 (1H, s),8.42 (1H, d,J=2.2Hz), 8.85 (1H, d,J=2.2Hz), 9.38 (1H, s); ESI-MS m/z 559.2 [(M+H)+]; HRMS(ESI) m/z calcd for C26H35N6O6S [(M+H)+]:559.2333, found: 559.2333 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice; | General procedure: Following the general procedure below, the data are reported as a) mass of starting material; b) mass of acid; c) mass of EDCI; d) volume of DCM; e) volume of NEt3; f) mass of product obtained.To an ice cold solution of corresponding primary amine 6a-d (0.05 - 0.38 mmol, 1 eq), corresponding acid (0.06 - 0.48 mmol, 1.3 eq) and EDCI (0.05 - 0.49 mmol, 1.3 eq) in DCM was added NEt3 (0.06 - 0.53 mmol, 1.4 eq) and the mixture was warmed to RT and stirred for 16 h. The reaction mixture was loaded directly onto a pre-equilibrated silica column and purified by silica gel column chromatography (gradient = 0-100% EtOAc in petroleum ether (bp. 40-60)). The appropriate fractions were combined and concentrated in vacuo to give the corresponding Boc-protected final compound 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | The title compound was prepared following the same procedure used for the synthesis of 12b, using pyridazine-3-caboxylic acid instead of 2-picolinic acid. Purification by preparative TLC afforded pure 12d as white solid (40%). MP = 136-137 C. 1H NMR (400 MHz, CDCl3) delta 1.46 (qd, J = 11.7, 3.2 Hz, 1H), 1.55-1.63 (m, 1H), 2.09-2.23 (m, 3H), 2.36-2.45 (m, 2H), 2.91 (dt, J = 14.2, 3.9 Hz, 1H), 4.21-4.29 (m, 1H), 6.32 (s, 1H), 6.97-7.02 (m, 3H), 7.10 (d, J = 7.6 Hz, 1H), 7.39 (t, J = 8.6 Hz, 1H), 7.66 (dd, J = 8.3, 4.9 Hz, 1H), 7.89 (dd, J = 8.6, 2.4 Hz, 1H), 8.15 (d, J = 8.4 Hz, 1H), 8.33 (dd, J = 8.6, 1.6 Hz, 1H), 8.44 (s, 1H), 9.27 (dd, J = 4.8, 1.6 Hz, 1H). MS (ESI) m/z 455.3 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 12h; | <strong>[2164-61-6]Pyridazine-3-carboxylic acid</strong> (0.190 g, 1.68 mmol) was added to the round bottom bottle in turn.EDCI (0.387g, 2.02mmol),DMAP (0.062g, 0.50mmol)And 10 ml of anhydrous N,N-dimethylformamide;Amino acid (0.5 g, 1.68 mmol) was further added, and the reaction was stirred at room temperature for 12 h.TLC (dichloromethane: methanol = 10:1) was found to be completely complete.The N,N-dimethylformamide was recovered under reduced pressure, and the residue was dissolved in 20 ml of dichloromethane.Wash with water (2 x 20 ml) and saturated brine (20 ml),Dry over anhydrous sodium sulfate, filter, and evaporate the solvent under reduced pressure.Separation on a silica gel column (eluent: chloroform:methanol = 20:1-10:1),Obtained 0.218 g of a tacrine-pyridazine conjugate (light yellow oil).The yield was 32% (see Figure 19 for the synthetic route and Figure 20 for the characterization map). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With acetic acid butyl ester; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 20 - 100℃; for 48.5h; | To a suspension of (3-bromopyridin-2-yl)methanamine hydrobromide (100 mg, 0.37 mmol) and the <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (60 mg, 0.49 mmol) in n-butyl acetate (5 mL), T3P (propylphosponic anhydride. 50% wt. in ethyl acetate; 2mL) was added and stirred at room temperature for about 30 min. The reaction mixture was heated at about 1 00C for about 48h. The reaction mixture was cooled, diluted with ethyl acetate, washed with sodium bicarbonate, water, brine and dried over sodium sulphate and concentrated. The residue was purified by prep HPLC using Gilson reverse phase eluting with ACN and water with 0.1% TF A using Luna column, to get the cyclized compound 8-bromo-3-(pyridazin-3yl)imidazo[1,5-a]pyridine (65 mg, 64% yield). 275.1 (M+1). |
Tags: 2164-61-6 synthesis path| 2164-61-6 SDS| 2164-61-6 COA| 2164-61-6 purity| 2164-61-6 application| 2164-61-6 NMR| 2164-61-6 COA| 2164-61-6 structure
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