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Search for reports by entering the product batch number.
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CAS No. : | 908240-50-6 |
Formula : | C7H3Cl2N3 |
M.W : | 200.02 |
SMILES Code : | ClC1=NC2=C(C=CN=C2)C(Cl)=N1 |
MDL No. : | MFCD10699461 |
Boiling Point : | No data available |
InChI Key : | YJUVYWACDUJBDG-UHFFFAOYSA-N |
Pubchem ID : | 45789969 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 47.35 |
TPSA ? Topological Polar Surface Area: Calculated from | 38.67 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.9 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.39 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.33 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 2.73 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 2.12 |
Log S (ESOL):? ESOL: Topological method implemented from | -3.2 |
Solubility | 0.125 mg/ml ; 0.000627 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.84 |
Solubility | 0.287 mg/ml ; 0.00143 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -4.19 |
Solubility | 0.0128 mg/ml ; 0.0000641 mol/l |
Class? Solubility class: Log S scale | Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -5.82 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.68 |
* 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 |
---|---|---|
67% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 3h; | After 2,4-dichloropyrido[3,4-d]pyrimidin (5 g, 24.9 mmol), phenylboronic acid (3.6 g, 29.9 mmol), Pd(PPh3)4 (1/15 g, 0.996 mmol), sodium carbonate aqueous solution (87 mL) , and ethanol (87 mL) were dissolved in toluene (180 mL), the mixture was stirred under reflux at 120 C for 3 hours. When the reaction was completed, an organic layer was extracted with ethyl acetate and remaining moisture was removed by using magnesium sulfate. Drying followed by column separation yielded Compound B-I (4 g, 16.5 mmol, 67 percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | 2-Chloro-N-(pyridin-4-ylmethyl)pyrido[3,4-d]pyrimidin-4-amine (B-3)To a solution of B-2 (500 mg, 2.50 mmol) in 12.5 mL of anhydrous DMF at RT under N2 was added 4-(aminomethyl)pyridine (0.278 mL, 2.75 mmol) followed by triethylamine (523 muL, 3.75 mmol). After stirring for several hours, the mixture was diluted with sat. aqueous NaHCO3 solution and extracted several times with EtOAc. The organic layers were combined and washed with sat. aqueous NaHCO3 solution, water, then brine, then dried with Na2SO4 and concentrated. The aqueous layers were combined and reextracted several times with 4:1 CHCl3-isopropanol; the organic layers were combined with the EtOAc extraction and concentrated. The residue was adsorbed onto silica gel and then purified by gradient elution on silica gel (0 to 100percent (25percent 20:1:1 EtOH:NH4OH:H2O-75percent EtOAc) in hexanes) to yield 426 mg (63percent) of B-3 as a dark brown solid. Data for B-3: 1HNMR (500 MHz, DMSO-d6) delta 9.71 (m, 1H), 9.05 (s, 1H), 8.68 (d, 1H), 8.52 (d, 2H), 8.20 (d, 1H), 7.37 (d, 2H), 4.80 (d, 2H) ppm. HRMS (ES) calculated M+H for C13H11ClN5: 272.0698. Found: 272.0696. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | 2,4-Dichloropyrido[3,4-d]pyrimidine (B-2)To a suspension of B-1 (500 mg, 2.8 mmol) in 6.5 mL (70 mmol) POCl3 was added DMF (32 muL, 0.4 mmol) and the mixture was heated in the microwave at 130° C. for 10 minutes. The reaction was transferred to a 250 mL round bottom flask with the help of DCM, and the volatiles were removed by rotary evaporation. The residue was suspended in 75 mL DCM and to this was carefully added 75 mL of 5percent aqueous Na2CO3 (pH>10 after addition). The layers were separated with the help of additional DCM, the organic was washed with water, dried over Na2SO4, and concentrated to provide 367 mg of a brown solid. This material was dissolved in DCM, dry loaded onto silica gel, and purified by column chromatography (0 to 100percent EtOAc in hexanes) to provide 148 mg (27percent) of B-2 as a white solid. Data for B-2: 1HNMR (500 MHz, CDCl3) delta 12.9 (s, 1H), 12.7 (s, 1H), 8.7 (s, 1H), 8.5 (d, 1H), 7.75 (d, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; at 25℃; for 18h; | To a mixture of pyrido[3,4-d]pyrimidine-2,4(1 H,3H)-dione (2b, 20.00 g, 122.60 mmol) and POCI3 (328.03 g, 2.14 mol) in toluene (200 mL) was added DIEA (31 .69 g, 245.20 mmol) dropwise and this reaction mixture stirred at 25°C overnight (18hr) to give suspension. The solvent and POCI3 was removed under vacuum, diluted with DCM (50 mL), neutralized with DIEA to pH=7 at -20°C and concentrated again, the residue was purified by column (20-50percent EA/PE) to give the product (2c, 20.00g, 99.99 mmol, 82percent yield) as a yellow solid. 1 H NMR (400 MHz, CHLOROFORM-d) delta 9.52 (s, 1 H), 8.92 (d, J=5.6 Hz, 1 H), 8.04 (d, J=5.6 Hz, 1 H). LCMS (m/z [M+H]+): 200.0. |
41% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene;Reflux; | To a mixture of pyrido[3,4-d]pyridine-2,4(1H,3H)-dione (2.0 g, 12.3 mmol) in toluene (50 mL) was added DIEA (3.15 g, 25 mmol) and POC13 (9.5 g, 61.4 mmol). The reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was taken in ethyl acetate, washed with aq. NaHCO3 and brine. The organics were dried and concentrated. The residue was purified by silica gel chromatography (25percent EA:PE)to give 1.0 g (41percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 9.50 (s, 1H), 8.90 (d, 1H, J 5.2 Hz), 8.02 (d, 1H, J 5.2 Hz). |
41% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene;Reflux; | [00156j To a mixture of pyrido[3,4-d]pyridine-2,4(1H,3H)-dione (2 g, 12.3 mmol) in toluene (50 mL) was added DIEA (3.15 g, 25 mmol) and POC13 (9.5 g, 61.4 mmol). The reaction mixture was refluxed overnight. The solution was concentrated in vacuo and the residue was taken in ethyl acetate and washed with aq. NaHCO3 and brine. The organics were dried and concentrated. The residue was purified by silica gel chromatography (25percent EA:PE) to afford lg (4 1percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 9.50 (s, 1H), 8.90 (d, 1H, J 5.2Hz), 8.02 (d, 1H, J 5.2Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With water; sodium hydroxide; In tetrahydrofuran; for 2h;Reflux; | To a solution of <strong>[908240-50-6]2,4-dichloropyrido[3,4-d]pyrimidine</strong> (1 g, 5 mmol) in THF (20 mL) was added a solution of NaOH (0.5 g, 12.5 mmol) in water (20 mL). The reaction mixture was stirred at rt for 2 h. The solution was adjusted to pH=2 using 5N HC1 and the resulting precipitate was filtered and washed with water and THF, and dried to give 0.8g (88percent) of the title compound. ?H NMR (400 MHz, DMSO-d6): oe 13.61 (s, 1H), 8.99 (s, 1H), 8.69 (d, 1H, J 5.2 Hz), 7.94 (d, 1H, J 5.2 Hz). |
88% | With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 2h; | [00157j To a solution of <strong>[908240-50-6]2,4-dichloropyrido[3,4-d]pyrimidine</strong> (1 g, 5 mmol) in THF (20 mL) was added a solution of NaOH (0.5 g, 12.5 mmol) in water (20 mL). The reaction mixture was stirred at r.t. for 2 h. The solution was adjusted to pH=2 using SN HC1 and the resulting precipitate was filtered and washed with water and THF, and dried to afford 0.8g (88percent) of the title compound.?H NMR (400 MHz, DMSO-d6): oe 13.61 (s, 1H), 8.99 (s, 1H), 8.69 (d, 1H, J 5.2 Hz), 7.94 (d, 1H, J 5.2 Hz). |
Tags: 908240-50-6 synthesis path| 908240-50-6 SDS| 908240-50-6 COA| 908240-50-6 purity| 908240-50-6 application| 908240-50-6 NMR| 908240-50-6 COA| 908240-50-6 structure
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