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CAS No. : | 1211536-93-4 | MDL No. : | MFCD17012952 |
Formula : | C6H3BrClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IYPTWTNEWAVBBM-UHFFFAOYSA-N |
M.W : | 232.47 | Pubchem ID : | 54758852 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.6 |
TPSA : | 41.57 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.01 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 2.4 |
Log Po/w (WLOGP) : | 2.37 |
Log Po/w (MLOGP) : | 1.13 |
Log Po/w (SILICOS-IT) : | 2.89 |
Consensus Log Po/w : | 2.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.4 |
Solubility : | 0.0928 mg/ml ; 0.000399 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.91 |
Solubility : | 0.283 mg/ml ; 0.00122 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.01 |
Solubility : | 0.0225 mg/ml ; 0.0000968 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.02 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane; water / 4 h / 110 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane; water / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane; water / 4 h / 110 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane; water / 3 h / 110 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4: triethylamine / tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane; water / 4 h / 110 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane; water / 3 h / 110 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2 h / 100 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 4h; Inert atmosphere; | The synthesis of tert-butyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-5,6- dihydropyridine-1(2H)-carboxylate To a solution of aryl bromide (233 mg, 1.0 mmol) in 1,4- dioxane (8 mL) and H2O (2 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-5,6-dihyropyridine-1(2H)-carboxylate (Eunkyung, K. et al Bioorganic & Medicinal Chemistry Letters 2008, 18, 4993-4996) (245 mg, 0.8 mmol), Pd(dppf)Cl2.DCM (41 mg, 0.05 mmol) and K2CO3(276 mg, 2.0 mmol) under N2. The mixture was stirred at 110 °C for 4 h, cooled to rt, diluted with H2O (80 mL) and extracted with EtOAc (60 mL x 3 . The organic layers separated, dried (Na2SO4) concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 5:1 to 2:1) to give the title compound (77 mg, yield 23%) as yellow solid ESI-MS (M+H)+: 335.2.1H NMR (400 MHz, CDCl3) : 10.82 (br, 1H), 8.71 (s, 1H), 6.73 (s, 1H), 6.68-6.56 (m, 1H), 4.16-4.13 (m, 2H), 3.70-3.65 (m, 2H), 2.62-2.60 (m, 2H), 1.46 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; | The synthesis of methyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate To a solution of aryl bromide (233 mg, 1.0 mmol) in 1,4- dioxane (8 mL) and H2O (2 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-5,6-dihyropyridine-1(2H)-carboxylate (Eunkyung, K. et al Bioorganic & Medicinal Chemistry Letters 2008, 18, 4993-4996) (245 mg, 0.8 mmol), Pd(dppf)Cl2.DCM (41 mg, 0.05 mmol) and K2CO3(276 mg, 2.0 mmol) under N2. The mixture was stirred at 110 °C for 4 h, cooled to rt, diluted with H2O (80 mL) and extracted with EtOAc (60 mL x 3 . The organic layers separated, dried (Na2SO4) concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 5:1 to 2:1) to give the title compound (77 mg, yield 23%) as yellow solid ESI-MS (M+H)+: 335.2.1H NMR (400 MHz, CDCl3) : 10.82 (br, 1H), 8.71 (s, 1H), 6.73 (s, 1H), 6.68-6.56 (m, 1H), 4.16-4.13 (m, 2H), 3.70-3.65 (m, 2H), 2.62-2.60 (m, 2H), 1.46 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere; | The synthesis of 4-chloro-6-(1-methyl-1H-pyrazol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine To a solution of aryl bromide (233 mg, 1.0 mmol) in 1,4- dioxane (8 mL) and H2O (2 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-5,6-dihyropyridine-1(2H)-carboxylate (Eunkyung, K. et al Bioorganic & Medicinal Chemistry Letters 2008, 18, 4993-4996) (245 mg, 0.8 mmol), Pd(dppf)Cl2.DCM (41 mg, 0.05 mmol) and K2CO3(276 mg, 2.0 mmol) under N2. The mixture was stirred at 110 °C for 4 h, cooled to rt, diluted with H2O (80 mL) and extracted with EtOAc (60 mL x 3 . The organic layers separated, dried (Na2SO4) concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 5:1 to 2:1) to give the title compound (77 mg, yield 23%) as yellow solid ESI-MS (M+H)+: 335.2.1H NMR (400 MHz, CDCl3) : 10.82 (br, 1H), 8.71 (s, 1H), 6.73 (s, 1H), 6.68-6.56 (m, 1H), 4.16-4.13 (m, 2H), 3.70-3.65 (m, 2H), 2.62-2.60 (m, 2H), 1.46 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water;Heating; Inert atmosphere; | To a solution of tert-butyl 4-(4-chloro-5H-pyrrolo[3,2- d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (67 mg, 0.2 mmol) in 1,4-dioxane (4 mL) and H2O (1 mL), was added 2-(tert-butyl)-N-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzyl)thiazole-5-carboxamide (83 mg, 0.2 mmol), Pd(dppf)Cl2.DCM (17 mg, 0.02 mmol) and K2CO3(55 mg, 0.4 mmol) under an atmosphere of N2. The mixture was stirred at 110 C for 3 h, cooled to rt, diluted with H2O (20 mL) and extracted with EtOAc (60 mL x 2 . The organic layers were collected, concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 1:1 to 1:2) to give the title compound (70 mg, yield: 60%) as yellow solid ESI-MS (M+H)+: 587.1.1H NMR (400 MHz, CD3OD) : 8.60 (br, 1H), 8.12 (s, 1H), 7.60-7.58 (m, 2H), 7.32-7.30 (m, 1H), 6.49 (s, 1H), 6.43-6.40 (m, 1H), 4.45 (s, 2H), 3.99-3.96 (m, 2H), 3.50-3.48 (m, 2H), 2.44-2.40 (m, 2H), 2.29 (s, 3H), 1.35 (s, 9H), 1.30 (s, 9H). |
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