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CAS No. : | 571189-23-6 | MDL No. : | MFCD11849292 |
Formula : | C14H22N4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ICNBTOYLGTVUCE-UHFFFAOYSA-N |
M.W : | 278.35 | Pubchem ID : | 75481723 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.57 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 85.84 |
TPSA : | 71.69 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.08 cm/s |
Log Po/w (iLOGP) : | 2.5 |
Log Po/w (XLOGP3) : | 1.29 |
Log Po/w (WLOGP) : | 0.97 |
Log Po/w (MLOGP) : | 0.98 |
Log Po/w (SILICOS-IT) : | 0.4 |
Consensus Log Po/w : | 1.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.34 |
Solubility : | 1.28 mg/ml ; 0.00461 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.4 |
Solubility : | 1.12 mg/ml ; 0.00402 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.35 |
Solubility : | 1.26 mg/ml ; 0.00452 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
83% | With sodium hydrogencarbonate In ethanol; water for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol for 7h; Heating; | |
223 mg | In N,N-dimethyl acetamide at 190℃; for 0.166667h; | 19.1 Step 1: preparation of tert-butyl 4-(2-amino-4-pyridyl)piperazine-1-carboxylate (compound 19b) A mixture of 4-chloropyridin-2-amine (compound 19a, CAS: 19798-80-2, Vendor: Aldrich, 129 mg, 1.00 mmol) and te rt- butyl piperazine- 1-carboxy late (CAS: 57260-71-6, Vendor: Accela ChemBio Inc, 186 mg, 1.00 mmol) in N,N-dimethylacetamide (3 mL) was heated at 190 °C for 10 minutes. After the reaction mixture was cooled down, the solid was collected by filtration to give compound 19b (223 mg) as a grey solid. MS: calc'd 279 (MH+), measured 279 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 2h; | 232 Preparation of tert-butyl 4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazine-1-carboxylate 11 (Example 232) A mixture of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (2.50 g, 8.49 rnmol), tert-butyl 4-(2-arninopyridin-4-yl)piperazine-1-carboxylate 10 (226 g, 809 mmol), and NaHCO3 (1.36 g, 16.18 mmol) in DMF (5 mL) was heated at 90°C for 2 h.The reaction mixture was cooled to room temperature and poured into water. The precipitate obtained was collected by filtration and washed with water, and dried under reduced pressure. The crude material was purified by column chromatography (silica gel,4% MeOH/DCM) to provide tert-butyl 4-[2-(5-chloro-2,4-dirnethoxyphenyl)imidazo[1,2-a]pyridin-7-ylpiperazine-1-carboxylate 11 (2.3 g, 60%) as a light yellow solid. 1H NMR (300 MHz, CDCl3): δ 836 (s, 1H), 7.90 (d, J = 7.5Hz, 1H), 7.88 (s, 1H),681 (d.J= 1.8 Hz, 1H), 658 (s, 1H), 6.54 (dd,J 2.3, 7.5Hz, 1 H), 3.99 (s. 3H), 3.95 (s,3 H), 3.60 (t, J= 49Hz, 4H), 3.18 (t, J= 5.2Hz, 4H), 1.49 (s, 9H); HPLC (Method 1) 96.6% (AUC), tR= 11.55 min; ESI MS m/z 473 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 80 °C 3: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 4: ammonium hydroxide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetone / 16 h / 75 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetone / 16 h / 75 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr 3: sodium t-butanolate / <i>tert</i>-butyl alcohol / 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetone / 16 h / 75 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr 3: sodium t-butanolate / <i>tert</i>-butyl alcohol / 4 h / 90 °C 4: hydrogenchloride / 1,4-dioxane / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.5h; | Preparation of tert-butyl 4-(2-amino-5-bromopyridin-4-yl)piperazine-1-carboxylate 123 To a solution of tert-butyl 4-(2-aminopyridin-4-yl)piperazine-1-carboxylate 122 (250 mg, 0,90 mmol) in DMF (5 mL) was added N-bromosuccinimide (160 mg, 0.90 mmol). The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with 10% sodium thiosulfate solution (100 mL) and extracted with chloroform (100 mL). The organic layer was concentrated under reduced pressure, and purified by column chromatography (silica gel, MeOH/DCM) to provide the desired compound iert-hutyi 4-(2-amino-5-bromopyridin-4-yl)piperazine-1-carboxylate 123 (150 mg, 47%) as a pale-yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 80 °C 3: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In acetone at 75℃; for 16h; | Preparation of tert-butyl 4-{2-[2-(benzyloxy)-5-chloro-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl}piperazine-1-carboxylate 31 A solution of 1-[2-(benzvloxy)-5-chloro-4-rnethoxyphenyl]-2-bromoethanone 30 (132 mg, 0.359 rnrnol) and tert-butyl 4-(2-aminopyridin-4-yl)piperazine- 1-carboxylate 10 (100 rng, 0.359 mmoi) in acetone (2 mL) was heated at 75°C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and washed with acetone. The solid was suspended in aqueous ammonia (10 rnL) and stirred for 2 h. The reaction mixture was filtered and dried under reduced pressure to give the desired compound tert-butyl 4-{2-[2-(benzyloxy)-5-chloro-4-methoxyphenyl]imidazo[1 ,2-a]pyridin-7-yl}piperazine-1-carboxylate 31(140 mg, 71 %) as a white solid. 1H NMR (300 MHz, CD3OD): δ 8.30 (d, J= 7.7 Hz, 1H), 7.99 (s, 1H), 7.77 (s, 1H), 7.52-7.46 (m, 2H), 7.45-7.31 (m, 3H), 7.15 (m. 1H). 6.69 (s, 1H). 6.79-6.74 (m, 1H), 5.40 (s, 2H), 390 (s, 3H), 3.67-3.51 (m, 8H), 1.49 (s. 9H); HPLC (Method 3) >99% (AUC). 6 =19.63 min.; ESI MS m/z 549 [M +H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.4% | With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 2h; | Preparation of tert-butyl 4-(2-(5-chloro-2-ethyl-4-methoxyphenyl)imidazo[l,2-a]pyridin-7-yl)piperazine-1 -carboxylate 104; A mixture of 2-bromo-1-(5-chloro-2-ethyl-4-methoxyphenyl)ethanone 103 (260 mg, 0.9()mmoi), tert-butyl 4-(2-aminopyridin-4-yl)piperazine-l-carboxylate (250 g, 0.90 mmol), and NaHCO3 (230 mg, 2.70 mmol) in DMF (5 mL) was heated at 90°C for 2 h. The reaction mixture was cooled to room temperature and poured into water. The precipitate so obtained was filtered, washed with water, and dried under reduced pressure. The precipitate was purified by column chromatography (silica gel, MeOH/DCM) to provide tert-butyl 4-(2-(5-chloro-2-ethyl-4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazine-1 -carboxylate 104 (300 mg, 71.4%) as a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine / <i>tert</i>-butyl alcohol; toluene / 110 °C / Inert atmosphere 2: trifluoroacetic acid / neat (no solvent) / 12 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; caesium carbonate In toluene; <i>tert</i>-butyl alcohol at 110℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 25℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 36 h / 60 °C 2: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 36 h / 60 °C 2: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16 mg | Stage #1: tert-butyl 4-(2-aminopyridin-4-yl)piperazine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: ((2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl)methyl trifluoromethanesulfonate With potassium carbonate In acetonitrile at 85℃; for 2h; | 19.2 Step 2: preparation of 5-[(2S,6R)-2-[[4-(2-amino-4-pyridyl)piperazin-1-yl]methyl]-6-methyl-morpholin-4-yl]quinoline-8-carbonitrile (Example 19) The mixture of tert-butyl 4-(2-amino-4-pyridyl)piperazine-1-carboxylate (compound 19b, 67 mg, 240 m mol) and DCM/TFA=l/2 (3 mL) was stirred at room temperature for 1 h, then it was concentrated and the residue was dissolved in ACN (6 mL), to which K2CO3 (83 mg, 600 m mol) and [(2R,6R)-4-(8-cyano-5-quinolyl)-6-methyl-morpholin-2-yl]methyl trifluoromethanesulfonate (Intermediate A, 83 mg, 200 miho) were added. After being stirred at 85 °C for 2 hrs, the reaction mixture was filtered and then directly purified by prep-HPLC to give Example 19 (16 mg). MS: calc'd 444 (MH+), measured 444 (MH+). 1 H NMR (400MHz, METHANOL-d4) d = 9.01 (dd, 7=1.6, 4.3 Hz, 1H), 8.68 (dd, 7=1.7, 8.6 Hz, 1H), 8.18 (d, 7=7.9 Hz, 1H), 7.67 (dd, 7=4.3, 8.6 Hz, 1H), 7.64 (d, 7=7.5 Hz, 1H), 7.30 (d, 7=7.9 Hz, 1H), 6.66 (dd, 7=2.6, 7.6 Hz, 1H), 6.17 (d, 7=2.4 Hz, 1H), 4.58 - 4.48 (m, 1H), 4.27 - 4.15 (m, 1H), 4.09 - 3.75 (m, 4H), 3.68 - 3.49 (m, 4H), 3.48 - 3.39 (m, 4H), 2.84 - 2.71 (m, 2H), 1.33 (d, 7=6.2 Hz, 3H). |
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