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CAS No. : | 128812-35-1 | MDL No. : | MFCD12924739 |
Formula : | C10H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VOQBTLZBLJPLNW-UHFFFAOYSA-N |
M.W : | 179.22 | Pubchem ID : | 15721843 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 49.5 |
TPSA : | 42.09 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) : | -5.9 cm/s |
Log Po/w (iLOGP) : | 2.16 |
Log Po/w (XLOGP3) : | 2.1 |
Log Po/w (WLOGP) : | 1.68 |
Log Po/w (MLOGP) : | 1.33 |
Log Po/w (SILICOS-IT) : | 2.79 |
Consensus Log Po/w : | 2.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.36 |
Solubility : | 0.781 mg/ml ; 0.00436 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.61 |
Solubility : | 0.436 mg/ml ; 0.00243 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.92 |
Solubility : | 0.217 mg/ml ; 0.00121 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.42 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
With potassium hydroxide for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With sodium ethanolate In ethanol for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. KOH / 0.5 h / Heating 2: 43 percent / H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / NEt3 / ethanol / 15 h / Ambient temperature 2: 10 percent / NaOEt / ethanol / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; rhodium on carbon; hydrogen In ethanol at 60℃; for 24h; | 3 Hydroqenation of the compound of formua (IIIa) Neat sufuric acid (1.1 g) and Rh/C (220 mg, 5w% Rh on actiyated charcoal) were added to a soution of the compound of formua (Ula) in EtOH (20 mL). The reaction mixture was hydrogenated at a pressure of 50 bar and a temperature of 60 °C. n this case the conyersion was approximatey 50% after 24 hours as determined by GC. After basic work-up (NaHCO3) spiking experiments and NMR experiments confirmed the formation of thecompound of formua (Va): The data of the compound of formua (iVa) are in compete agreement with the data obtained in experiment 6 (deprotection of the compound of formua (Via)). | |
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 3 h / 20 °C 2: rhodium on carbon; hydrogen; triethylamine / ethanol / 1 h / 60 °C / 7500.75 Torr / Autoclave 3: hydrogenchloride; water / dichloromethane / 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 3 h / 20 °C 2: rhodium on carbon; hydrogen; triethylamine / ethanol / 1 h / 60 °C / 7500.75 Torr / Autoclave |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid; rhodium on carbon; hydrogen / ethanol / 24 h / 60 °C / 37503.8 Torr 2: acetonitrile / 16 h / 4 °C / Resolution of racemate | ||
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 3 h / 20 °C 2: rhodium on carbon; hydrogen; triethylamine / ethanol / 1 h / 60 °C / 7500.75 Torr / Autoclave 3: hydrogenchloride; water / dichloromethane / 40 °C 4: acetonitrile / 16 h / 4 °C / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dmap; triethylamine In dichloromethane at 20℃; for 3h; | 2 BOC-Protection of the compound of formula (IIIa) Triethylamine (70.7 g, 699 mmol) and Boc2O (30.75 g, 141 mmol) were added to a stirred solution (ula) (12.5 g, 70 mmol) and dimethylaminopyridine (0.85 g, 7 mmol) indichloromethane (700 mL) at room temperature. The reaction mixture was stirred for three hours and the reaction progress was monitored by HPLC. The reaction was quenched by the addition of H20 (280 mL), the organic phase was separated and washed two more times with H20 (280 mL each) and brine (280 mL). The combined aqueous iayers were extracted with dichloromethane (280 mL) and the combined organic phases were dried oyer Na2SO4.After filtration the solution was concentrated under reduced pressure at 30 °C and the residue was dried in yacuum oyernight to giye 20.1 g crude product which was purified by flash coumn chromatography (300 g siica gel, heptane/ethy acetate = 30/1) to giye the compound of formua (Va). Yield: 19.1 g (98%).The compound of formua (Va) has the foowing spectroscopic data: 1H NMR of CCIO1-96-C (300 MHz, CDCI3): = 6.97 (s, 1H, NCH), 4.27 (q, J= 7.1 Hz, 2H, OCH2), 2.75 (t, J= 7.3 Hz,2H, CH2), 2.58 (t, J = 7.2 Hz, 2H, CH2), 2.29 (quint, J = 7.2 Hz, 2H, CH2), 1 .56 (s, 9H, tort.Bu), 1.33 (t, J = 7.1 Hz, 3H, CH3); 13C NMR of CCIO1-096-C (75 MHz, CDCI3): = 160.8, 148.9, 145.3, 132.0, 118.3, 117.2, 83.7, 60.2, 30.5, 27.7, 26.3, 24.5, 14.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: Ethyl isocyanoacetate With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-cyclopenten-1-yl phenyl sulfone In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere; | 1 Preparation of the compound of formula (IIa) The formation of the compound of formula (IIla) was done as follows: a solution of the compound of formula (Ia) (36.0 g, 318 mmol) in tetrahydrofuran (THF) (635 mL) was added within 15 minutes to a stirred suspension of potassium tert.-butoxide (47.5 g, 423 mmol) in dry THF (1279 mL) at O °C under N2-atmosphere and stirring was continued for 15 minutes. A solution of the compound of formula (Ma) (52.2 g, 251 mmol) in THF (1253 mL) was thenadded within 20 minutes and the reaction mixture was stirred at O °C for 10 minutes and at room temperature for 180 minutes. The reaction progress was monitored by HPLC. The reaction was quenched by the addition of H20 (1566 mL) and dichloromethane (1566 mL) was added. HCI (5.0 M, 153 g) were added in order to adjust the pH-yalue of the solution from pH = 13.0 to pH = 1.0. The two phases were separated and the organic iayer waswashed with NaOH (0.5 M, 2.2 L). The solyent was remoyed under reduced pressure at 40°C and the residue was dried in yacuum at room temperature. The crude product (46.6 g) was recrystallized: Heptane (373 mL) was added and the solution was warmed to 75 0C. The hot solution was filtered (K150) and then slowly cooled to O °C. The compound of formula (Ula) was filtered (G3 futer) and dried under reduced pressure at room temperature. Yield:38.7 g (86%).The compound of formula (ula) has the foiiowing spectroscopic data: 1H NMR (300 MHz,CDCI3): 6 9.06 (yery br. s, 1H, NH), 6.59 (d, J = 2.4 Hz, 1H, NCH=c), 4.30 (q, J = 7.1 Hz,2H, OCH2), 2.83 (t, J = 7.2 Hz, 2H, CH2), 2.64 (t, J = 7.2 Hz, 2H, CH2), 2.34 (quint, J 7.2Hz, 2H, CH2), 1.34 (t, J = 7.1 Hz, 3H, CH3); 13C NMR (75 MHz, CDCI3): 6 = 161.5, 138.4,132.1, 114.8, 114.7, 59.8, 31.0, 26.2, 24.9, 14.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 4: potassium hydroxide / ethylene glycol / 1.5 h / Reflux 5: trichlorophosphate / 1,2-dichloro-ethane / 2 h / 20 °C / Cooling with ice 6: sodium tetrahydroborate; methanol / dichloromethane / 1 h / Reflux 7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 4: potassium hydroxide / ethylene glycol / 1.5 h / Reflux 5: trichlorophosphate / 1,2-dichloro-ethane / 2 h / 20 °C / Cooling with ice 6: sodium tetrahydroborate; methanol / dichloromethane / 1 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 4: potassium hydroxide / ethylene glycol / 1.5 h / Reflux 5: trichlorophosphate / 1,2-dichloro-ethane / 2 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 4: potassium hydroxide / ethylene glycol / 1.5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N-iodo-succinimide In tetrahydrofuran at 20℃; | 4 Step 4: Synthesis of Compound BB-54-4 Compound BB-54-3 (1 g, 5.58 mmol) was dissolved in THF (20 mL), NIS (1.51 g, 6.70 mmol) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with saturated brines (20 mL×2), the organic phase was dried over anhydrous sodium sulfate. After filtration, the solvent was removed under reduced pressure, the concentrated liquid was separated by silica gel column chromatography (eluting reagent: 8% EtOAc/PE) to deliver the target compound BB-54-4 (1.57 g, 92%). LCMS m/z: 306.0 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: N-iodo-succinimide / tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 3 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 4: potassium hydroxide / ethylene glycol / 1.5 h / Reflux 5: trichlorophosphate / 1,2-dichloro-ethane / 2 h / 20 °C / Cooling with ice 6: sodium tetrahydroborate; methanol / dichloromethane / 1 h / Reflux 7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / dichloromethane / 1 h / 20 °C 8: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran; water; N,N-dimethyl-d<SUB>6</SUB>-formamide / 4 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.5h; Cooling with ice; | 3 Step 3: Synthesis of Compound BB-54-3 Under an ice bath, a solution of compound BB-54-2 (5 g, 22.49 mmol) and ethyl isocyanoacetate (6.42 g, 56.23 mmol) in THF (30 mL) was dripped slowly into a solution of NaH (2.25 g, 56.23 mmol) in THF (50 mL). The reaction mixture was stirred for 1 h at 0° C. and then stirred for further 30 min at room temperature. The reaction was quenched with methanol, the solvent was removed under reduced pressure, the concentrated liquid was subject to silica gel column chromatography (eluting reagent: 12% EtOAc/PE) to deliver the target compound BB-54-3 (3 g, 74%). 1H NMR (400 MHz, CDCl3) δ: 8.70 (br, 1H), 6.57 (s, 1H), 4.30-4.25 (m, 2H), 2.83-2.80 (m, 2H), 2.65-2.61 (m, 2H), 2.38-2.33 (m, 2H), 1.34-1.31 (m, 3H). |
72% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 82.25h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 1 h / 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Cooling with ice | ||
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0.52 h / 20 °C 2: sodium hydride / tetrahydrofuran / 82.25 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: iodine / dichloromethane; water / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 1 h / 20 °C 3: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Reflux; | 2.2.50 827 L of a 2.5 M solution in THF) at 0 °C was slowly added a solution of ethyl 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-1-carboxylate (0.686 mmol, 123 mg) in THF (3.00 mL). The reaction mixture was warmed up to r.t., then heated to reflux for 1 h. It was then cooled to r.t., saturated aqueous solution of potassium sodium tartrate (10.0 mL) and CH2Cl2 (10.0 mL) were added and the mixture was stirred for 16 h at r.t. before it was extracted with CH2Cl2 (3 x 10.0 mL). The combined organics were dried (MgSO4) and concentrated under reduced pressure. Flash chromatography gave 44 mg of compound 50.1 (53% yield) as a yellow oil.1H NMR (400 MHz, Chloroform-d) d 7.56 (br s, 1H), 6.30 (s, 1H), 2.63 (t, J = 7.1Hz, 2H), 2.54 (t, J = 7.1Hz, 2H), 2.31 (apparent p, J = 7.2 Hz, 2H), 2.19 (s, 3H); 13C NMR (101 MHz, Chloroform- d) d 130.5, 127.0, 118.3, 106.8, 31.8, 25.1, 24.0, 11.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Reflux 2.1: toluene-4-sulfonic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere 2.2: 0.25 h / 0 °C 2.3: 0.75 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrabutylammomium bromide; toluene-4-sulfonic acid In dichloromethane at 50℃; Inert atmosphere; Sealed tube; |
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