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CAS No. : | 25063-69-8 | MDL No. : | MFCD00170987 |
Formula : | C13H14N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RRLXNXFZXSSOGO-UHFFFAOYSA-N |
M.W : | 278.26 | Pubchem ID : | 4255799 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.31 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 68.9 |
TPSA : | 86.75 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.8 cm/s |
Log Po/w (iLOGP) : | 2.66 |
Log Po/w (XLOGP3) : | 1.68 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 1.45 |
Consensus Log Po/w : | 1.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.65 |
Solubility : | 0.626 mg/ml ; 0.00225 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.12 |
Solubility : | 0.213 mg/ml ; 0.000765 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.36 |
Solubility : | 0.121 mg/ml ; 0.000434 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.95 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | 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 |
---|---|---|
95% | In ethanol for 1h; Reflux; Large scale; | 1.i 1.i. 5-[{(6-methoxypyridin-3-yl)amino}methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione A double jacketed flask was charged with 5-amino-2-methoxypyridine (500 g, 1 eq.), 2,2-dimethyl-1,3-dioxane-4,6-dione (697 g, 1.2 eq.), triethylorthoformate (740 mL, 1.1 eq.) and ethanol (4 L). The mixture was heated to reflux for one hour. The dark suspension obtained was cooled to 5°C and the mixture was filtered. The product was washed with ethanol (1 L) and dried on a rotary evaporator to obtain a purple solid (1058 g; 95% yield). 1H-NMR (CDCl3): δ = 11.20 (d, J= 13.9 Hz, 1H), 8.51 (d, J= 14.2 Hz, 1H), 8.14 (d,J = 2.9 Hz, 1H), 7.54 (dd, J = 8.9, 3.0 Hz, 1H), 6.85 (d, J = 8.9 Hz, 1H), 3.98 (s, 3H),1.77 (s, 6H). LC-MS: tR = 1.22 min; [M+1]+ = 279; purity: 100% ala. |
95% | In ethanol for 1h; Reflux; Large scale; | |
95% | In ethanol for 1h; Reflux; Large scale; | 1.1.i 1.i. 5-(((6-methoxypyridin-3-yl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 1.i. 5-(((6-methoxypyridin-3-yl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione A double jacketed flask was charged with 5-amino-2-methoxypyridine (500 g, 1 eq.), 2,2-dimethyl-1,3-dioxane-4,6-dione (697 g, 1.2 eq.), triethylorthoformate (740 mL, 1.1 eq.) and ethanol (4 L). The mixture was heated to reflux for one hour. The dark suspension obtained was cooled to 5° C. and the mixture was filtered. The product was washed with ethanol (1 L) and dried on a rotary evaporator to obtain a purple solid (1058 g; 95% yield). 1H-NMR (CDCl3): δ=11.20 (d, J=13.9 Hz, 1H), 8.51 (d, J=14.2 Hz, 1H), 8.14 (d, J=2.9 Hz, 1H), 7.54 (dd, J=8.9, 3.0 Hz, 1H), 6.85 (d, J=8.9 Hz, 1H), 3.98 (s, 3H), 1.77 (s, 6H). LC-MS: tR=1.22 min; [M+1]+=279; purity: 100% a/a. |
91% | In ethanol at 20℃; for 51h; Heating / reflux; | 1.B.a A mixture of 6-(methoxy)-3-pyridinamine (50g, 403 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (68g, 472 mmol) and triethylorthofonnate (66g, 446 mmol) in ethanol (300 ml) was heated to reflux for 3 hours, then left for 2 days at room temperature. Filtration and drying afforded a white solid (102g, 91%). |
90% | In ethanol for 3h; Heating / reflux; | A.A 2-(6-Methoxy-[1,5]naphthyridin-4-yl)4,5,6,7-tetrahydro-2H-indazol-5-ylamine A. 5-[(6-Methoxy-pyridin-3-ylamino)-methylenel-2,2-dimethyl-[1,3]dioxane-4,6-dione. To a solution of 5-amino-2-methoxypyridine (37.2 g, 0.300 mol) in EtOH (225 mL) was added 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) (51 g, 350 mmol) and triethyl orthoformate (44.5 g, 0.300 mol). The mixture was heated to reflux and stirred for 3 h. The resulting suspension was cooled to RT, filtered, washed with EtOH (200 mL) and dried in vacuo to provide 75 g (90%) of the title compound as a tan solid. 1H NMR (500 MHz, DMSO-d6): 11.26 (d, J=14.6, 1H), 8.45 (d, J=14.6, 1H), 8.38 (d, J=2.9, 1H),7.97 (dd, J=8.9, 2.9, 1H), 6.88 (d, J=8.9, 1H), 3.86 (s, 3H), 1.67 (s, 6H). |
90% | In ethanol for 5h; Reflux; | 5-[(6-Methoxy-pyridin-3-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione 6-methoxypyridin-3-amine (25 g, 201.61 mmol) was dissolved in ethanol (150 mL), and isopropylidene malonate(31.9g, 221.77 mmol) and triethyl orthoformate (29.84 g, 201.61 mmol) were added, and the reaction solution was heated to reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and a large amount of solid was precipitated and filtered. The filter cake was washed with ethanol and dried to afford a dark brown solid (90.4 g, yield 90%). 1H-NMR (CDCl3, 400 MHz): δ 8.51 (d, J = 14.4Hz, 1H), 8.13 (d, J = 2.8 Hz, 1H), 7.54-7.51 (m, 1H), 6.84 (d, J= 8.8 Hz, 1H), 3.95 (s, 3H), 1.75 (s, 6H). |
89% | ||
84.77% | In ethanol at 85℃; for 4h; | 146 Example 146.3-[(3-chloro-2-methoxyphenyl)amino]-2-(6-cyclopropyl-1,5-naphthyridin- 4-yl)-1H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one (compound 752) Into a 500-mL round-bottom flask, was placed 5-amino-2-methoxypyridine (10.00 g, 80.55 mmol, 1.00 equiv), ethyl alcohol (100 mL), meldrum (11.61 g, 80.55 mmol, 1.00 equiv), triethyl orthoformate (11.94 g, 80.55 mmol, 1.00 equiv). The resulting solution was stirred for 4 h at 85 . The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The precipitated solids were collected by filtration and washed with EtOH (3x30 mL) to afford 5-[[(6-methoxypyridin-3- yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (19.00 g, 84.77%) as an off- white solid. LC-MS: (M+H)+ found: 279.0 |
In ethanol for 2h; Heating / reflux; | 46 To a solution of 5-amino-2-methoxypyridine (1 Ig) in ethanol (15OmL) was added 2,2- dimethyl-l,3-dioxane-4,6-dione (16g) and triethyl orthoformate (15mL). After heating at reflux for 2 hours, the mixture was cooled in an ice bath, filtered and the solids were washed with methanol to give 5-[(6-methoxypyridin-3-yl)amino]methylene}-2,2-dimethyl-l,3-dioxane-4,6- dione (23g). | |
In ethanol at 80℃; for 3h; Inert atmosphere; | A1.a Preparation of intermediate 1 Under argon atmosphere, meldrum's acid (108 g, 752 mmol) and triethyl orthoformate (108 ml, 651 mmol) were added to a solution of 5-amino-2-methoxypyridine (62.2 g, 501 mmol) in ethanol (210 ml). The mixture was stirred at 80°C for 3 hours and then cooled to room temperature and stirred overnight. The precipitate was filtered off, washed with ethanol (2 x 200 ml) and then was dried to afford 138 g (99%) of intermediate 1 , that was used without further purification for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In diphenylether at 260℃; | |
85% | In diphenyl ether-biphenyl eutectic at 250 - 260℃; for 0.233333h; | A.B 2-(6-Methoxy-[1,5]naphthyridin-4-yl)4,5,6,7-tetrahydro-2H-indazol-5-ylamine B. 6-Methoxy-[1,5]naphthyridin-4-ol. Dowtherm A (26.5:73.5 diphenyl/diphenyl oxide) (140 mL) was added to a three-neck flask fitted with an air-condenser, thermocouple and a funnel and the solvent was heated to 260° C. To the Dowtherm A was added 5-[(6-methoxy-pyridin-3-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (34.8 g, 125 mmol) over a period of 10 min, keeping the temperature above 250° C. The funnel was rinsed with Dowtherm A (20 mL). The reaction mixture was heated for a further 4 min and then removed from the heat source. The resulting suspension was cooled to RT and treated with Et2O (200 mL). The-solid was filtered, washed with Et2O (300 mL), hexanes (500 mL) and dried in vacuo to provide 18.8 g (85%) of the title compound as a tan solid. 1H NMR (500 MHz, DMSO-d6): 11.88 (br s, 1H), 8.13 (br s, 2H), 7.17 (s, 1H), 6.22 (br s, 1H), 3.93 (s, 3H). |
68% | With 1,3-dimethyl-2-imidazolidinone at 80 - 255℃; for 0.583333h; Inert atmosphere; | 1.ii 1. ii. 6-methoxy-], 5-naph thyridin-4-ol. Dowtherm A (1300 mL) was heated to 255°C under nitrogen atmosphere with the help of an electrical heating mantle. Intermediate 1.i (161 g, 1 eq.) was dissolved in 1,3-dimethyl- imidazolidinone (500 mL) at 80°C. The solution was added to the boiling Dowtherm A over a period of about 35 mm. The reaction mixture was cooled to 20°C. The mixture was filtered and slurried in ethanol (800 mL) at 80°C. The mixture was cooled to 20°C, filtered and washed with ethanol (150 mL). The product was dried on a rotary evaporator at 50°C and below 5 mbar to yield a brown solid (69.6 g; 68% yield). 1H-NMR (d6-DMSO): δ = 11.78 (m, 1H), 7.97 (m, 2H), 7.17 (d, J = 9.0 Hz, 1H), 6.28 (m, 1H), 3.94 (s, 3H). LC-MS: tR = 0.49 min; [M+1]+ = 177; purity: 99% a/a. |
68% | With 1,3-dimethyl-2-imidazolidinone; Dowtherm A at 80 - 255℃; | |
68% | With 1,3-dimethyl-2-imidazolidinone at 80 - 255℃; for 0.583333h; Inert atmosphere; | 1.1.ii 1.ii. 6-methoxy-1,5-naphthyridin-4-ol 1.ii. 6-methoxy-1,5-naphthyridin-4-ol Dowtherm A (1300 mL) was heated to 255° C. under nitrogen atmosphere with the help of an electrical heating mantle. Intermediate 1.i (161 g, 1 eq.) was dissolved in 1,3-dimethyl-imidazolidinone (500 mL) at 80° C. The solution was added to the boiling Dowtherm A over a period of about 35 min. The reaction mixture was cooled to 20° C. The mixture was filtered and slurried in ethanol (800 mL) at 80° C. The mixture was cooled to 20° C., filtered and washed with ethanol (150 mL). The product was dried on a rotary evaporator at 50° C. and below 5 mbar to yield a brown solid (69.6 g; 68% yield). 1H-NMR (d6-DMSO): δ=11.78 (m, 1H), 7.97 (m, 2H), 7.17 (d, J=9.0 Hz, 1H), 6.28 (m, 1H), 3.94 (s, 3H). LC-MS: tR=0.49 min; [M+1]+=177; purity: 99% a/a. |
60% | With diphenyl ether-biphenyl eutectic at 190℃; for 0.5h; | 6-Methoxy-[1,5] naphthyridin-4-ol Diphenyl ether-biphenyl eutectic (170 mL) was heated to 190 °C,. 5-[(6-methoxy-pyridine-3-ylamino)-methylene]-2,2-dimethyl-[l,3]dioxan-4,6-dione (17 g, 61.5 mmol) was added to the above solution in batches, then the reaction solution was maintained at 190 °C and stirred for 0.5 h. After the reaction was completed, the reaction solution was cooled to room temperature, and diethyl ether (170 mL) was added, a large amount of solid was precipitated and filtered. The filter cake was washed with diethyl ether and dried to afford a brown solid (6.5 g, yield 60%). MS (ESI): m/z = 177 [M+H]+. |
In diphenylether for 0.416667h; Heating / reflux; | 46 5-[(6-Methoxypyridin-3-yl)amino]methylene}-2,2-dimethyl-l,3-dioxane-4,6-dione (23g) was added in small portions to refluxing phenyl ether and stirred for 25 minutes. The mixture was then cooled to room temperature and diethyl ether (10OmL) was added. The solids were filtered, suspended in diethyl ether, stirred at room temperature for 30 minutes and filtered again to give 4-hydroxy-6-methoxy-l,5-naphthyridine (10.4g). | |
In diphenylether at 220℃; for 0.166667h; | A1.b Preparation of intermediate 2 Intermediate 1 (13.6 g, 49.6 mmol) was added portionwise to diphenyl ether (100 ml, 630 mmol) at 220°C. The solution was stirred at reflux for 10 minutes and then cooled to room temperature. The combined precipitated solid were filtered off and washed with diethyl ether (2 x 500 ml) to give 45.6 g of a pale brown solid. The solid was triturated in diethyl ether (2 x 500 ml), filtered off and dried under vacuum to give 44g (50%) of intermediate 2, that was used without further purification for the next step. | |
27.3 g | With diphenyl ether-biphenyl eutectic at 240℃; for 0.0833333h; | Step 2M.1 M.2M.l (54. Og) was added portionwise to Dowtherm A (320 mL) (Sigma-Aldrich, St. Louis, MO) at 240 °C for 5 minutes. After cooling, the resulting precipitates were collected by filtration and washed with diethyl ether to give M.2 (27.3 g). 1H NMR (DMSO-de): δ 3.93 (s, 3H), 6.23 (brs, 1H), 7.15 (d, J= 8.6 Hz, 1H), 7.94 (d, J= 8.6 Hz, 1H), 8.65 (d, J= 2.4 Hz, 1H), 11.72 (brs, 1H). |
In diphenylether; biphenyl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 86 percent / diphenyl ether; various solvent(s) / 260 °C 2: NH2NH2 / 1-methyl-pyrrolidin-2-one / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 86 percent / diphenyl ether; various solvent(s) / 260 °C 2: NH2NH2 / 1-methyl-pyrrolidin-2-one / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 86 percent / diphenyl ether; various solvent(s) / 260 °C 2: NH2NH2 / 1-methyl-pyrrolidin-2-one / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 86 percent / diphenyl ether; various solvent(s) / 260 °C 2.1: NH2NH2 / 1-methyl-pyrrolidin-2-one / 140 °C 3.1: tetrahydrofuran 3.2: p-TsOH / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 86 percent / diphenyl ether; various solvent(s) / 260 °C 2.1: NH2NH2 / 1-methyl-pyrrolidin-2-one / 140 °C 3.1: tetrahydrofuran 3.2: p-TsOH / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In diphenylether at 220℃; | |
74% | With Dowtherm A for 0.166667h; Heating / reflux; | 1.B.b Meldrum's adduct (1a Method B) (51g, 183 mmol) was added portionwise over 5 minutes to refluxing Dowtherm A (300ml) (NB Dowtherm A is a commercially available eutectic mixture comprising 26.5% biphenyl and 73.5% biphenyl ether). After the addition was complete, heating was continued for a further 5 minutes then allowed to cool to room temperature. The solution was added to ether (600 ml) and the resulting suspension filtered affording a pale brown solid (24g, 74%). MS (APCI+) m/z 177 (MH+). |
64% | With diphenylether; biphenyl at 220℃; |
50% | With 1,3-dimethyl-2-imidazolidinone for 0.25h; Inert atmosphere; Heating; | |
In diphenylether; biphenyl at 220℃; for 1h; | 121 5-Amino-2-methoxy-pyridine (1.26 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (2.06 g) were suspended in 2-propanol (40 ml), and the suspension was stirred at 70°C for 30 min. The reaction mixture was cooled to room temperature, and the precipitated crystal was then collected by filtration and was washed with methanol and then with ether. The crystal thus obtained as such was used in the next reaction without further purification. The crystal prepared above and biphenyl (5.1 g) were suspended in diphenyl ether (20 ml), and the suspension was stirred at 220°C for one hr. The reaction mixture was cooled to room temperature, and the reaction mixture was then filtered and was washed with chloroform. The residue as such was used in the next reaction without further purification. | |
In diphenylether at 250℃; for 0.333333h; Inert atmosphere; | 4.2 6-Methoxy-1,5naphthyridin-4(1H)-one Step 2: 6-Methoxy-1,5naphthyridin-4(1H)-one A suspension of 5-((6-methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dione-4,6-dione (51.3 g, 0.185 μmol) in diphenylether (1275 mL) was heated to 250° C. under nitrogen atmosphere for 20 min. The reaction mixture was cooled to RT and diluted with hexane. The gummy solid was then triturated with hexane to obtain 6-methoxy-1,5-naphthyridin-4(1H)-one as a pale brown color solid. | |
In diphenylether at 250℃; for 0.333333h; | 4.2 Step 2: 6-Methoxy-L5-naphthyridin-4(lH)-one; A suspension of 5-((6-methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-l,3-dioxane- 4,6-dione (51.3 g, 0.185 mol) in diphenylether (1275 mL) was heated to 250 °C under nitrogen atmosphere for 20 min. The reaction mixture was cooled to RT and diluted with hexane. The gummy solid was then triturated with hexane to obtain 6-methoxy-l,5- naphthyridin-4(lH)-one as a pale brown color solid. | |
In diphenylether; biphenyl at 220℃; for 0.0833333h; | 13 A portion (0.5 g) of the material so obtained was added portionwise to a mixture (28 ml) of biphenyl and diphenyl ether ('Dowtherm A') that had been warmed to 22O0C and the resultant mixture was stirred at 2200C for 5 minutes. The mixture was cooled to ambient 0 temperature. The precipitate was isolated, washed with petroleum ether and dried under vacuum. There was thus obtained 6-methoxy-4-oxo-l,4-dihydro-l,5-naphthyridine (0.245 g); 1H NMR Spectrum: (CDCl3) 4.09(s, 3H), 7.04 (d, IH), 7.16 (d, IH)5 8.22 (d, IH), 8.56 (d, IH); Mass Spectrum: M+H1" 177 (which material is also described in International Patent Application WO 2004/041210, at page 24 thereof). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In isopropyl alcohol Heating; | |
In isopropyl alcohol at 70℃; for 0.5h; | 121 5-Amino-2-methoxy-pyridine (1.26 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (2.06 g) were suspended in 2-propanol (40 ml), and the suspension was stirred at 70°C for 30 min. The reaction mixture was cooled to room temperature, and the precipitated crystal was then collected by filtration and was washed with methanol and then with ether. The crystal thus obtained as such was used in the next reaction without further purification. The crystal prepared above and biphenyl (5.1 g) were suspended in diphenyl ether (20 ml), and the suspension was stirred at 220°C for one hr. The reaction mixture was cooled to room temperature, and the reaction mixture was then filtered and was washed with chloroform. The residue as such was used in the next reaction without further purification. | |
In isopropyl alcohol for 1h; Heating / reflux; | 13 The 4-chloro-6-methoxy-l,5-naphthyridine used as a starting material was prepared as follows :- o 5-(Methoxymethylidene)-2,2-dimethyl-l,3-dioxane-4,6-dione (0.7 g) was added portionwise to a stirred solution of 3-amino-6-rnethoxypyridine (0.516 g) in isopropanol (4 ml). The resultant mixture was stirred and heated to reflux for 1 hour. The mixture was cooled to ambient temperature. The precipitate was isolated and washed with isopropanol. There was thus obtained 5-[(6-methoxypyridin-3-ylamino)methylidene]-2,2-dimethyl- 5 l,3-dioxane-4,6-dione (1.04 g); 1H NMR Spectrum: (CDCl3) 1.76 (s, 6H), 3.96 (s, 3H), 6.82 (d, IH), 7.51 (m, IH), 8.12 (d, IH), 8.48 (d, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate In ethanol at 105℃; for 2h; Stage #2: 6-methoxy-pyridin-3-ylamine In ethanol at 105℃; for 12h; | |
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate at 105℃; for 2h; Stage #2: 6-methoxy-pyridin-3-ylamine at 105℃; | 4.1 5-((6-Methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione Step 1:5-((6-Methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione A mixture of Meldrum's acid (34.8 g, 0.242 μmol) and trimethyl orthoformate (285 mL, 2.05 μmol) was heated to 105° C. for 2 h. To the solution 6-methoxypyridin-3-amine (30 g 0.242 μmol) was added and continued the stirring overnight at the same temperature. The mixture was allowed to cool to RT and diluted with hexane. The solid precipitated was filtered and washed with hexane to afford 5-((6-methoxypyridin-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione as a pale yellow solid. | |
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate at 105℃; for 2h; Stage #2: 6-methoxy-pyridin-3-ylamine at 105℃; | 4.1 Example 4Synthesis of 8-Chloro-2-methoxy-l,5-naphthyridine Step 1 : 5-((6-Methoxypyridin-3-ylamino)methylene)-2.2-dimethyl- 1.3-dioxane-4,6-dione; A mixture of Meldrum's acid (34.8 g, 0.242 mol) and trimethyl orthoformate (285 mL, 2.05 mol) was heated to 105 °C for 2 h. To the solution 6-methoxypyridin-3 -amine (30 g, 0.242 mol) was added and continued the stirring overnight at the same temperature. The mixture was allowed to cool to RT and diluted with hexane. The solid precipitated was filtered and washed with hexane to afford 5-((6-methoxypyridin-3-ylamino)methylene)- 2,2-dimethyl-l,3-dioxane-4,6-dione as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2: nitric acid / 4.33 h / 67 °C 3: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 65 °C | ||
Multi-step reaction with 3 steps 1: 1,3-dimethyl-2-imidazolidinone; Dowtherm A / 80 - 255 °C 2: nitric acid 3: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C | ||
Multi-step reaction with 3 steps 1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2: nitric acid / 4.33 h / 10 - 67 °C 3: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2: nitric acid / 4.33 h / 67 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 0.83 h / 25 °C | ||
Multi-step reaction with 3 steps 1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2: nitric acid / 4.33 h / 10 - 67 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 0.83 h / 20 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 67 °C 3.1: trichlorophosphate / N,N-dimethyl-formamide / 0.83 h / 25 °C 4.1: hydrogen / methanol / 2.5 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 12 h / 50 °C / 7500.75 Torr / Autoclave | ||
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 67 °C 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 3 h / 50 °C / 7500.75 Torr / Autoclave | ||
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone; Dowtherm A / 80 - 255 °C 2.1: nitric acid 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr 4.2: Raney nickel / 50 °C / 7500.75 Torr |
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 10 - 67 °C 3.1: trichlorophosphate / N,N-dimethyl-formamide / 0.83 h / 20 - 25 °C 4.1: hydrogen / methanol / 2.5 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 12 h / 50 °C / 7500.75 Torr | ||
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 10 - 67 °C 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 3 h / 50 °C / 7500.75 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 67 °C 3.1: trichlorophosphate / N,N-dimethyl-formamide / 0.83 h / 25 °C 4.1: hydrogen / methanol / 2.5 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 12 h / 50 °C / 7500.75 Torr / Autoclave 5.1: boron trifluoride diethyl etherate; tert.-butylnitrite / tetrahydrofuran / 0.25 h / -20 - 25 °C 5.2: 85 °C | ||
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 67 °C 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 3 h / 50 °C / 7500.75 Torr / Autoclave 5.1: boron trifluoride diethyl etherate; tert.-butylnitrite / tetrahydrofuran / 0.25 h / -20 - 25 °C 5.2: 85 °C | ||
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone; Dowtherm A / 80 - 255 °C 2.1: nitric acid 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr 4.2: Raney nickel / 50 °C / 7500.75 Torr 5.1: hydrogen fluoride; sodium nitrite / tetrahydrofuran / -50 - 10 °C |
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 10 - 67 °C 3.1: trichlorophosphate / N,N-dimethyl-formamide / 0.83 h / 20 - 25 °C 4.1: hydrogen / methanol / 2.5 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 12 h / 50 °C / 7500.75 Torr 5.1: pyridine; hydrogen fluoride / 0.17 h / -50 - -40 °C 5.2: 1 h / -9 - 10 °C 5.3: 0.5 h / -30 - 65 °C / Autoclave | ||
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.58 h / 80 - 255 °C / Inert atmosphere 2.1: nitric acid / 4.33 h / 10 - 67 °C 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr / Autoclave 4.2: Raney nickel / 3 h / 50 °C / 7500.75 Torr 5.1: pyridine; hydrogen fluoride / 0.17 h / -50 - -40 °C 5.2: 1 h / -9 - 10 °C 5.3: 0.5 h / -30 - 65 °C / Autoclave |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With cycl-isopropylidene malonate In ethanol for 2h; Reflux; | |
157 g | With cycl-isopropylidene malonate In ethanol for 1h; Reflux; | Intermediate M8-Bromo-7-chloro-2-methox - 1 ,5 -naphthyridineA mixture of J.l (87.9 g), Meldrum's acid (120 g) and triethyl orthoformate (105 mL) in ethanol (527 mL) was heated under reflux for 1 hour. The resulting precipitates were collected by filtration and washed with ethanol to give M.l (157 g).1H NMR (CDC13): δ 1.76 (s, 6H), 3.96 (s, 3H), 6.83 (d, J= 8.6 Hz, 1H), 7.52 (dd, J= 8.6, 3.1 Hz, 1H), 8.12 (d, J= 3.1 Hz, 1H), 8.49 (d, J= 14.1 Hz, 1H), 11.18 (d, J= 14.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone; Dowtherm A / 80 - 255 °C 2.1: fluorine; silica gel; sulfuric acid / 27 h / 80 °C 2.2: 2 h / 0 - 20 °C / pH 7.4 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1 h / 50 - 70 °C 4.1: n-hexyllithium / tetrahydrofuran; hexane / 1 h / -78 - -70 °C 4.2: -78 - 20 °C | ||
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone; Dowtherm A / 80 - 255 °C 2.1: nitric acid 3.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.25 h / 20 - 65 °C 4.1: hydrogen / methanol / 2 h / 3750.38 Torr 4.2: Raney nickel / 50 °C / 7500.75 Torr 5.1: hydrogen fluoride; sodium nitrite / tetrahydrofuran / -50 - 10 °C 6.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -75 - -70 °C 6.2: 1 h / -74 - -72 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: N-[2'-(dicyclohexylphosphino)-1,1'-biphenyl-2-yl]-N,N-dimethylamine; tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3 / 1,4-dioxane / 18 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3 / 1,4-dioxane / 0.17 h / Inert atmosphere; Sonication 3.2: 18 h / 85 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: N-[2'-(dicyclohexylphosphino)-1,1'-biphenyl-2-yl]-N,N-dimethylamine; tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3 / 1,4-dioxane / 18 h / 100 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3 / 1,4-dioxane / 0.17 h / Inert atmosphere; Sonication 3.2: 18 h / 85 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C 4.2: 0.17 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: hydrogen; palladium on activated charcoal / methanol / 16 h / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: trifluoroacetic acid / dichloromethane / 16 h 5.2: 0.17 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: hydrogen; palladium on activated charcoal / methanol / 16 h / 50 °C / Inert atmosphere 6.1: piperidine / methanol / 16 h / Molecular sieve; Reflux 6.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: trifluoroacetic acid / dichloromethane / 16 h 5.2: 0.17 h 6.1: piperidine / methanol / 16 h / Molecular sieve; Reflux 6.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: N-[2'-(dicyclohexylphosphino)-1,1'-biphenyl-2-yl]-N,N-dimethylamine; tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3 / 1,4-dioxane / 18 h / 100 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h 5.1: triethylamine / N,N-dimethyl-formamide; water monomer / 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3 / 1,4-dioxane / 0.17 h / Inert atmosphere; Sonication 3.2: 18 h / 85 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C 4.2: 0.17 h 5.1: triethylamine / N,N-dimethyl-formamide; water monomer / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone / 0.25 h / Inert atmosphere; Heating 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / Inert atmosphere; Cooling with ice 2.2: 16 h / 20 °C / Inert atmosphere 3.1: 1-aminopropane hydrochloride; pyridine / 16 h / Reflux 4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h 4.2: 16 h / 50 °C 5.1: palladium on activated charcoal / ethanol / 16 h / 50 °C / Inert atmosphere 6.1: triethylamine / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Heating 2: Heating 3: NBS / Cooling 4: ammonium acetate / ethanol / 18 h / 20 - 50 °C | ||
Multi-step reaction with 5 steps 1: biphenyl / diphenylether / 0.25 h / 250 °C 2: phosphorus tribromide / N,N-dimethyl-formamide / 1 h / 0 - 45 °C / Inert atmosphere 3: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 4: NBS / tetrahydrofuran; lithium hydroxide monohydrate / 0.33 h / 20 °C 5: ammonium acetate / ethanol / 18 h / 20 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Heating 2: Heating 3: NBS / Cooling 4: ammonium acetate / ethanol / 18 h / 20 - 50 °C 5: N-iodo-succinimide / N,N-dimethyl-formamide / 16 h / 20 °C | ||
Multi-step reaction with 6 steps 1: biphenyl / diphenylether / 0.25 h / 250 °C 2: phosphorus tribromide / N,N-dimethyl-formamide / 1 h / 0 - 45 °C / Inert atmosphere 3: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 4: NBS / tetrahydrofuran; lithium hydroxide monohydrate / 0.33 h / 20 °C 5: ammonium acetate / ethanol / 18 h / 20 - 50 °C 6: N-iodo-succinimide / N,N-dimethyl-formamide / 16 h / 20 °C |
Tags: 25063-69-8 synthesis path| 25063-69-8 SDS| 25063-69-8 COA| 25063-69-8 purity| 25063-69-8 application| 25063-69-8 NMR| 25063-69-8 COA| 25063-69-8 structure
[ 25063-68-7 ]
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H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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