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CAS No. : | 915302-21-5 | MDL No. : | MFCD13189444 |
Formula : | C7H4ClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LEIGIRAWJADGAI-UHFFFAOYSA-N |
M.W : | 165.58 | Pubchem ID : | 11958054 |
Synonyms : |
|
Num. heavy atoms : | 11 |
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 : | 42.34 |
TPSA : | 38.67 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) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 1.82 |
Log Po/w (XLOGP3) : | 1.52 |
Log Po/w (WLOGP) : | 1.68 |
Log Po/w (MLOGP) : | 0.66 |
Log Po/w (SILICOS-IT) : | 2.12 |
Consensus Log Po/w : | 1.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.5 |
Solubility : | 0.527 mg/ml ; 0.00318 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.94 |
Solubility : | 1.9 mg/ml ; 0.0115 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.56 |
Solubility : | 0.0453 mg/ml ; 0.000274 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.55 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
86% | With sodium carbonate In ethanol; toluene at 100℃; for 3h; | |
86% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 100℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium carbonate In ethanol; toluene at 100℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium carbonate In ethanol; toluene at 100℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium carbonate In ethanol; toluene at 100℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium carbonate In ethanol; toluene at 100℃; for 2h; | |
85% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 100℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 100 percent / AlCl3 / methoxybenzene / 2 h / 20 °C 2: 58 percent / POCl3; PCl5 / 4 h / Heating 3: 86 percent / Bu3SnH / Pd(PPh3)4 / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 72 percent / 48 h / Heating 2: Et3N / tetrahydrofuran / 1.5 h / -10 °C 3: NaN3 / tetrahydrofuran; H2O / 1.5 h / 0 °C 4: toluene / 2 h / Heating 5: pyridine / toluene / 24 h / Heating 6: 100 percent / AlCl3 / methoxybenzene / 2 h / 20 °C 7: 58 percent / POCl3; PCl5 / 4 h / Heating 8: 86 percent / Bu3SnH / Pd(PPh3)4 / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 58 percent / POCl3; PCl5 / 4 h / Heating 2: 86 percent / Bu3SnH / Pd(PPh3)4 / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / toluene / 24 h / Heating 2: 100 percent / AlCl3 / methoxybenzene / 2 h / 20 °C 3: 58 percent / POCl3; PCl5 / 4 h / Heating 4: 86 percent / Bu3SnH / Pd(PPh3)4 / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: toluene / 2 h / Heating 2: pyridine / toluene / 24 h / Heating 3: 100 percent / AlCl3 / methoxybenzene / 2 h / 20 °C 4: 58 percent / POCl3; PCl5 / 4 h / Heating 5: 86 percent / Bu3SnH / Pd(PPh3)4 / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: NaN3 / tetrahydrofuran; H2O / 1.5 h / 0 °C 2: toluene / 2 h / Heating 3: pyridine / toluene / 24 h / Heating 4: 100 percent / AlCl3 / methoxybenzene / 2 h / 20 °C 5: 58 percent / POCl3; PCl5 / 4 h / Heating 6: 86 percent / Bu3SnH / Pd(PPh3)4 / toluene / 1 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.25h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With ammonium hydroxide In tetrahydrofuran at 80℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.333333h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 100℃; for 3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.25h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.166667h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.25h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In 1,4-dioxane for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In 1,4-dioxane for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In 1,4-dioxane for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In 1,4-dioxane for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In 1,4-dioxane for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In 1,4-dioxane for 48h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.75h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane for 0.25h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 0.33 h / 210 °C 2.1: trichlorophosphate; phosphorus pentachloride / 6 h / Reflux 3.1: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) / toluene / 1 h / 100 °C / Inert atmosphere 3.2: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With triethylamine In 1,4-dioxane Reflux; | 1 N-(3,4-dichlorobenzyl)pyrido[3,2-d]pyrimidin-2-amine (4) Product 3 (100 mg, 0.60 mmol) was dissolved in 1,4-dioxane (7 mL) and the successive addition was made of 3,4-dichlorobenzylamine (0.10 mL, 0.75 mmol, 1.2 eq.) and triethylamine (0.11 mL, 0.79 mmol, 1.5 eq.), and the mixture refluxed under stirring overnight. The 1,4-dioxane was evaporated and the residue obtained taken up in water (20 mL) and extracted with dichloromethane (2×20 mL). The combined organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The reaction product was chromatographed on silica gel (gradient EP to EP/ acOEt 50:50) to give the title product 4 (110 mg, 60%) in the form of a yellow solid. Rf (EP/acOEt 60:40): 0.13. 1H NMR (400 MHz, CdCl3) δ 9.20 (s, 1H), 8.66 (dd, J=4.1, 1.4 Hz, 1H), 7.89 (d, J=8.5 Hz, 1H), 7.57 (dd, J=8.6, 4.1 Hz, 1H), 7.50 (d, J=1.5 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 1.7 Hz, 1H), 5.93 (s, 1H), 4.73 (d, J=6.2 Hz, 2H). 13C NMR (101 MHz, CdCl3) δ 163.7, 159.3, 148.3, 147.5, 139.5, 137.2, 133.9, 132.8, 131.4, 130.7, 129.6, 128.5, 127.0, 44.8. IR (diamond aTR cm-1) ν 3231, 3034, 2862, 1585, 1541, 1465, 1397, 1351, 1250, 1142, 1035, 936, 821. HRMS (EI-MS) m/z calculated for C14H10Cl2N4 [M+H]+: 305.035528; found: 305.035355. Tm: 163-165° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trichlorophosphate; phosphorus pentachloride / 6 h / Reflux 2.1: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) / toluene / 1 h / 100 °C / Inert atmosphere 2.2: 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; Inert atmosphere; | A.55.1 Step 1: To a solution of 2-chloropyrido[3,2-d]pyrimidine (120 mg, 0.72 mmol) in dioxane (5 mL) and water (0.5 mL) were added 5,6-difluoro-1-(oxan-2-yl)indazol-3- ylboronic acid (245 mg, 0.87 mmol), [1,T- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (53 mg, 0.07 mmol) and potassium carbonate (300 mg, 2.17 mmol). The mixture was stirred at 100 °C overnight under nitrogen atmosphere. The mixture was concentrated under vacuum. The residue was purified by flash column chromatography with 0-20% ethyl acetate in petroleum ether to afford 5,6-difluoro-1-(oxan-2-yl)-3-[pyrido[3,2-d]pyrimidin-2-yl]indazole (250 mg, 93%) as an off-white solid. MS m/z 368.1 [M+1]+. |
93% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; Inert atmosphere; | A.55.1 Step 1: To a solution of 2-chloropyrido[3,2-d]pyrimidine (120 mg, 0.72 mmol) in dioxane (5 mL) and water (0.5 mL) were added 5,6-difluoro-1-(oxan-2-yl)indazol-3- ylboronic acid (245 mg, 0.87 mmol), [1,T- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (53 mg, 0.07 mmol) and potassium carbonate (300 mg, 2.17 mmol). The mixture was stirred at 100 °C overnight under nitrogen atmosphere. The mixture was concentrated under vacuum. The residue was purified by flash column chromatography with 0-20% ethyl acetate in petroleum ether to afford 5,6-difluoro-1-(oxan-2-yl)-3-[pyrido[3,2-d]pyrimidin-2-yl]indazole (250 mg, 93%) as an off-white solid. MS m/z 368.1 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 100 °C / Inert atmosphere 2: Adams’s catalyst; hydrogen / methanol / 20 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 100 °C / Inert atmosphere 2: Adams’s catalyst; hydrogen / methanol / 20 °C |
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