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CAS No. : | 1375110-97-6 | MDL No. : | MFCD24645609 |
Formula : | C8H9N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VWVRRNUIGQUURB-UHFFFAOYSA-N |
M.W : | 147.18 | Pubchem ID : | 60145038 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.56 |
TPSA : | 43.32 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) : | -6.15 cm/s |
Log Po/w (iLOGP) : | 1.55 |
Log Po/w (XLOGP3) : | 1.48 |
Log Po/w (WLOGP) : | 1.23 |
Log Po/w (MLOGP) : | 0.44 |
Log Po/w (SILICOS-IT) : | 0.68 |
Consensus Log Po/w : | 1.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.29 |
Solubility : | 0.754 mg/ml ; 0.00512 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.0 |
Solubility : | 1.48 mg/ml ; 0.0101 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.09 |
Solubility : | 1.19 mg/ml ; 0.00807 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / 100 h / Reflux 2: hydrogenchloride; sodium nitrite / water / 5 - 20 °C 3: Reflux 4: water; sodium hydroxide / 17 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite / water / 5 - 20 °C 2: Reflux 3: water; sodium hydroxide / 17 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With water; sodium hydroxide for 17h; Reflux; | 4.1.9. General method for the synthesis of 2-substituted 7-aminooimidazo[1,2-a]pyridine derivatives 26(g-j) General procedure: A stirred solution of the appropriate carbamate 25(g-j) (2.0 g, 9.76 mmol) in 5 N aqueous NaOH (100 mL) was refluxed for 7 h. After cooled to room temperature, the solution was diluted with H2O (100 mL), extracted with CH2Cl2 (3 × 50 mL), dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified on neutral alumina eluted with (CH2Cl2/EtOH, 99/1, v/v) to afford the appropriate amine 26(g-j). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 21 h / Reflux 2: trichlorophosphate / 6 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In toluene for 21h; Reflux; | 4.1.10. General method for the synthesis of ethyl N-(imidazo[1,2-a]pyridin-7-yl)aminomethylenemalonate 27(f-j) and N-(imidazo[1,2-a]pyridin-8-yl)aminomethylenemalonate 31(g-j) derivatives General procedure: Diethyl ethoxymethylenemalonate (7.0 g, 32.0 mmol) was added to a stirred solution of the corresponding amine 5, 26(f-i), 30(f-i) (20.0 mmol) in dry toluene. The mixture was refluxed for 10 h and then cooled to room temperature. After removal of the solvent, the residue was purified by chromatography (alumina/CH2Cl2) to provide compound 27(f-j) or 31(g-j). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Reflux 2: water; sodium hydroxide / 17 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 3h; | 27 Example 27 6-(4-((5-chloro-2-((2-methylimidazo[1,2-a]pyridin-7-yl)amino)pyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile To a suspension of 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-l- yl)pyridazine-3 -carbonitrile (0.15 g, 0.43 mmol) in anhydrous l,4-dioxane (10 mL) were added 2-methylimidazo[l,2-a]pyridin-7-amine (0.097 g, 0.66 mmol), Pd(OAc)2 (0.020 g, 0.087 mmol), BINAP (0.055 g, 0.089 mmol) and Cs2C03 (0.30 g, 0.92 mmol). The mixture was degassed and refilled with N2 for several times and then heated to 100 °C and stirred for 3 h. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/(a solution of NH3 in MeOH (3M)) (v/v) = 100/1 to 50/1 to 30/1), to give the crude product. The crude product was stirred with EtOAc (3 mL), filtered and the filter cake was collected and dried in vacuo to afford the title compound as a white solid (95 mg, yield 48%).MS (ESI, pos. ion) m/z: 461.2 [M+H]+;HRMS (ESI, pos. ion) m/z: 461.1716 [M+H]+, calculated value for C22H22CIN10 [M+H]+ is 461.1712;1H NMR (400 MHz, DMSO-^) d (ppm): 9.51 (s, 1H), 8.26 (d, J = 7.3 Hz, 1H), 8.08-8.01 (m, 2H), 7.88 (d, J= 9.7 Hz, 1H), 7.49-7.40 (m, 2H), 7.06 (dd, J= 7.4, 1.9 Hz, 1H), 7.02 (d, J= 7.8 Hz, 1H), 4.70-4.58 (m, 2H), 4.45-4.32 (m, 1H), 3.29-3.20 (m, 2H), 2.24 (s, 3H), 2.12-2.01 (m, 2H), 1.77-1.62 (m, 2H);13C NMR (100 MHz, DMSO-^): d 159.11, 158.21, 157.26, 153.81, 145.85, 142.40, 137.78, 131.58, 128.82, 126.16, 117.94, 111.63, 108.73, 107.14, 104.63, 100.49, 48.68, 44.33, 30.91, 14.81. |
48% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; | 27 Example 27 6-(4-((5-Chloro-2-((2-methylimidazo[1,2-a]pyridin-7-yl)amino)pyrimidin-4-yl)amino)piperidine- 1-yl)pyridazine-3-carbonitrile To 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile (0.15 g, 0.43 mmol)Anhydrous 1,4-dioxane (10 mL)Into the suspension2-methylimidazo[1,2-a]pyridin-7-amine (0.097 g, 0.66 mmol),Pd(OAc) 2 (0.020 g, 0.087 mmol),BINAP (0.055g, 0.089mmol)And Cs2CO3 (0.30 g, 0.92 mmol).The reaction mixture is exhausted of air,And filled with nitrogen several times,Raise the temperature to 100 ° C and stir the reaction for 3 hours.It was then concentrated under reduced pressure.The residue was purified by silica gel column chromatography (EtOAc EtOAc EtOAcThe crude product was obtained.The resulting crude was stirred in EtOAc (3 mLThe collected filter cake is dried under reduced pressure.The title compound was obtained as a white solid (95 mg, yield 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / water / 12 h / Reflux 2: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 80 °C 3: hydrogenchloride / ethyl acetate / 7 h / 20 °C | ||
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / water / 12 h / Reflux 2: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 80 °C 3: hydrogenchloride / ethyl acetate / 7 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane Reflux; | 8.5 Step 5) tert-butyl 4-((5-chloro-2-((2-methylimidazo[1,2-a]pyridin-7-yl)amino)pyrimidin-4-yl)(methyl)amino)-3-ethylpiperidine-1-carboxylate A mixture of /er/-butyl 4-((2,5-dichloropyrimidin-4-yl)(methyl)amino)-3- ethylpiperidine-l-carboxylate (208 mg, 0.5343 mmol), 2-methylimidazo[l,2-a]pyridin-7-amine (70 mg, 0.47561 mmol), Pd(OAc)2 (11.5 mg, 0.0512 mmol), BINAP (28.6 mg, 0.0459 mmol) and Cs2C03 (316.7 mg, 0.9720 mmol) was dissolved in l,4-dioxane (15 mL). The reaction mixture was heated to reflux and stirred overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH(v/v) = 40/1) to give the title compound as a yellow solid (140 mg, yield 58%).MS (ESI, pos. ion) m/z: 500.3 [M+H]+. |
58% | With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane Reflux; | 8.5 Step 5) 4-((5-Chloro-2-((2-methylimidazo[1,2-a]pyridin-7-yl)amino)pyrimidin-4-yl)(methyl)amino)-3 -ethyl piperidine-1-carboxylic acid tert-butyl ester will4-((2,5-dichloropyrimidin-4-yl)(methyl)amino)-3-ethylpiperidine1-carboxylate(208 mg, 0.5343 mmol),2-methylimidazo[1,2-a]pyridine-7-amine (70 mg, 0.47561 mmol),Pd(OAc) 2 (11.5 mg, 0.0512 mmol),BINAP (28.6 mg, 0.0459 mmol) and Cs2CO3 (316.7 mg, 0.9720 mmol)The mixture was dissolved in 1,4-dioxane (15 mL).The resulting mixture was warmed to reflux and stirred overnight.After the reaction was completed, it was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc / EtOAcThe title compound was obtained as a yellow solid (140 mg, yield 58%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 80 °C 2: hydrogenchloride / ethyl acetate / 7 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With hydrogenchloride In ethyl acetate at 20℃; for 7h; | 8.4 Step 4) 2-methylimidazo[1,2-a]pyridin-7-amine A mixture of N-(diphenylmethylene)-2-methylimidazo[l,2-a]pyridin-7-amine (580 mg, 1.863 mmol) in a solution of hydrogen chloride in EtOAc (20 mL, 30 mmol, 1.5 M) was stirred at rt for 7 hours and then washed with water (50 mL x 2). The combined aqueous layers were adjusted to pH = 10 with saturated Na2C03 aqueous solution, and the resulting mixture was extracted with a mixed solvent of DCM/MeOH (10/1 (v/v), 150 mL x 4). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/(a solution of NH3 in MeOH (7M)) (v/v) = 40/1 ) to give the title compound as a light yellow solid (90 mg, yield 33%).MS (ESI, pos. ion) m/z: 148.20 [M+H]+; 1H NMR (400 MHz, CDCl3) d (ppm): 7.73 (d, J= 7.2 Hz, 1H), 7.05 (s, 1H), 6.56 (d, J= 1.6 Hz, 1H), 6.19 (dd, j= 7.2, 2.2 Hz, 1H), 3.91 (s, 2H), 2.34 (s, 3H). |
33% | With hydrogenchloride In ethyl acetate at 20℃; for 7h; | 8.4 Step 4) 2-Methylimidazo[1,2-a]pyridin-7-amine N-(Diphenylmethylene)-2-methylimidazo[1,2-a]pyridine-7-amine (580 mg, 1.863 mmol)Hydrogen chloride was added to EtOAc (20 mL, 30 mmol, 1.5 M) solution,The resulting mixture was stirred at room temperature for 7 hours.It was then washed with water (50 mL x 2).The combined aqueous phases were adjusted to pH = 10 with saturated aqueous Na 2CO 3.The resulting mixture was treated with DCM/MeOHThe mixed solvent (10/1 (v/v), 150 mL x 4) was extracted.The combined organic phases were dried over anhydrous sodium sulfate.Filter and concentrate under reduced pressure.The residue obtained was subjected to silica gel column chromatography(DCM/NH3 in MeOH (7M) (v/v) = 40/1)To give the title compound as a pale yellow solid (90mg, 33% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / Reflux 2: hydrogenchloride / ethyl acetate / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / Reflux 2: hydrogenchloride / ethyl acetate / 1 h / 20 °C 3: triethylamine / ethanol / 20 °C | ||
Multi-step reaction with 3 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate; palladium diacetate / 1,4-dioxane / Reflux 2: hydrogenchloride / ethyl acetate / 1 h / 20 °C 3: triethylamine / ethanol / 20 °C |