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CAS No. : | 100189-16-0 | MDL No. : | MFCD06637422 |
Formula : | C8H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LYMOQGXOROSRPJ-UHFFFAOYSA-N |
M.W : | 137.18 | Pubchem ID : | 10129989 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.14 |
TPSA : | 33.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 1.81 |
Log Po/w (XLOGP3) : | 0.77 |
Log Po/w (WLOGP) : | 1.12 |
Log Po/w (MLOGP) : | 0.55 |
Log Po/w (SILICOS-IT) : | 1.79 |
Consensus Log Po/w : | 1.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.55 |
Solubility : | 3.83 mg/ml ; 0.028 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.05 |
Solubility : | 12.3 mg/ml ; 0.09 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 0.784 mg/ml ; 0.00571 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
To a stirring solution of 1-(6-methyl-3-pyridinyl)ethanone (1.0 g, 7.4 mmol) in absolute ethanol (10 ml) at 0 0C was added sodium borohydride (0.14 g, 3.7 mmol) portionwise over 20 minutes. The reaction mixture was stirred at 0 0C for 1.5 hours before warming to room temperature. The mixture was partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate. The organic phase was dried over sodium sulphate, filtered, and evaporated in vacuo to give the crude product 1-(6-methyl-3- pyridinyl) ethanol (810 mg).1H-NMR (400MHz, CDCI3): delta 8.45 (1 H, s), 7.63 (1 H, m), 7.14 (1 H, d, J=8Hz), 4.93 (1 H, m), 2.54 (3H, s), 2.09 (1 H, bs), 1.53 (3H, m). | ||
17 g | With sodium tetrahydroborate; ethanol; at 0℃; for 1.5h; | Sodium borohydride (2.3 g, 0.06 mol) was added in small portions over 30 mm, to a solution of compound 1(16.4 g, 0.121 mol) in ethanol (160 ml) at 0C and the reactionmixture was stirred at same temperature. After 1 h, the reaction mixture was diluted with sodium bicarbonate solution (sat) (2x200 ml) and extracted with dichloromethane (2x500 ml). The combined organic extract was dried over anhydrous sodium sulphate and concentrated to afford a pale yellow oil, which was purified by flash column chromatography (5% methanol/dichloromethane) to afford compound 11(17.0 g; 93% yield over 2 steps) as a pale yellow oil.ES-MS [M+1]+: 138.11H NMR (400 MHz, CDCI3): 68.35 (d, J = 2.0 Hz, 1H), 7.63 (dd, J = 8.0, 2.4 Hz, 1H),7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (brs, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H) |
17 g | With sodium tetrahydroborate; ethanol; at 0℃; for 1.5h; | Sodium borohydride (2.3 g, 0.06 mol) was added in small portions over 30 min, to a solution of compound 2a (16.4 g, 0.121 mol) in ethanol (160 mL) at 0C and the reaction mixture was stirred at same temperature. After 1 h, the reaction mixture was diluted with sodium bicarbonate solution (sat) (2x200 mL) and extracted with dichloromethane (2x500 mL). The combined organic extract was dried over anhydrous sodium sulphate and concentrated to afford a pale yellow oil, which was purified by flash column chromatography (5% methanol/dichloromethane) to afford compound 3a (17.0 g; 93% yield over 2 steps) as a pale yellow oil. ES-MS [M+l]+: 138.1. 1H NMR (400 MHz, CDC13): delta 8.35 (d, J = 2.0 Hz, 1H), 7.63 (dd, J = 8.0, 2.4 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 4.89 (q, J = 6.5 Hz, 1H), 3.30 (br s, 1H), 2.50 (s, 3H), 1.48 (d, J = 6.5 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Compound II (15 g, 0.109 mol) was added, drop wise, to a cooled suspension ofsodium hydride (6.56 g, 0.164 mol) in tetrahydrofurane (150 ml) and stirred at 0C.After 30 mi chloromethyl methyl ether (13.2 g, 0.164 mol) was added drop wise while stirring and keeping the internal temperature around 0C. After addition is over, the reaction mixture was stirred at the same temperature for 1 h. The reaction was quenched with ice cold water (80 ml) and extracted with ethyl acetate (3x50 ml). Thecombined organic extract was dried over anhydrous sodium sulphate and concentrated to afford an orange color oil, which was purified by flash column chromatography (1% methanol/dichloromethane) to afford compound III (10.0 g; 51% yield) as a pale yellow oil.ES-MS [M+1]+: 182.21H NMR (400 MHz, CDCI3): 6 8.45 (d, J = 2.0 Hz, 1H), 7.56 (dd, J = 8.0, 2.0 Hz, 1H),7.14 (d, J = 8.0 Hz, 1H), 4.75 (q, J = 6.4 Hz, 1H), 4.57 (ABq, 2H), 3.36 (s, 3H), 2.53 (s,3H), 1.48 (d, J = 6.6 Hz, 3H) | |
51% | Compound 3a (15 g, 0.109 mol) was added, drop wise, to a cooled suspension of sodium hydride (6.56 g, 0.164 mol) in tetrahydrofurane (150 mL) and stirred at 0C. After 30 min, chloromethyl methyl ether (13.2 g, 0.164 mol) was added drop wise while stirring and keeping the internal temperature around 0C. After addition is over, the reaction mixture was stirred at the same temperature for 1 h. The reaction was quenched with ice cold water (80 mL) and extracted with ethyl acetate (3x50 mL). The combined organic extract was dried over anhydrous sodium sulphate and concentrated to afford an orange color oil, which was purified by flash column chromatography (1% methanol/dichloromethane) to afford compound 4a (10.0 g; 51% yield) as a pale yellow oil. ES-MS [M+l]+: 182.2. 1H NMR (400 MHz, CDC13): delta 8.45 (d, J = 2.0 Hz, 1H), 7.56 (dd, J = 8.0, 2.0 Hz, 1H), 7.14 (d, J = 8.0 Hz, 1H), 4.75 (q, J = 6.4 Hz, 1H), 4.57 (ABq, 2H), 3.36 (s, 3H), 2.53 (s, 3H), 1.48 (d, J = 6.6 Hz, 3H). | |
In N,N-dimethyl-formamide; | Reference Example 1 Sodium hydride in oil (60%, 7.0 g) was added with ice-cooling to a solution of <strong>[56019-64-8]5-(1-hydroxyethyl)-2-methylpyridine</strong> (20.0 g) in N,N-dimethylformamide (120 ml). The mixture was stirred for 15 minutes. Then, chloromethyl methyl ether (14.1 g) was added dropwise at the same temperature. The reaction mixture was further stirred for 30 minutes with ice-cooling. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and subjected to distillation under reduced pressure to obtain 5-(1-methoxymethoxyethyl)-2-methylpyridine (21.5 g, yield: 81%), b.p. 78-80 C./0.8 mmHg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-Methyl-5-(1-chlor-ethyl)-pyridin, sied. K-Acetat/H2O, K2CO3; | ||
2-Methyl-5-acetylpyridine, H2 (71-75 kg/cm2), Raney-Ni, dioxane, 110grad; | ||
I (/BRN= 109608/), H2 (75 kg/cm2), Raney-Ni, dioxane, 120grad; with 2-methyl-5-ethyl-pyridine <XII>; |
2-Methyl-5-(1-chlor-ethyl)-pyridin, sd. wss. K-Acetat, K2CO3; | ||
entspr. Pyridin, 1) Chlor, hν, 2) NaOH, H2O; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 2: 27 percent / H2O / 5 h / 160 °C 3: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature | ||
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C | ||
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: potassium carbonate / toluene; ethanol / 5 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1.) NaH / 1.) hexane, DMF, 0 deg C, 1.5 h, 2.) hexane, DMF, from -78 deg C to RT 2: 27 percent / H2O / 5 h / 160 °C 3: 62 percent / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 18 h / Ambient temperature 4: 58 percent / piperidine / ethanol / 18 h / Heating | ||
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C 5.1: piperidine; ethanol / 15 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, 19 min, 2.) DMF, 30 min 2: 32 percent / H2O / 8 h / 150 - 160 °C 3: 71 percent / NaH / dimethylformamide / 1 h 4: H2 / 5percent Pd/C / ethyl acetate / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 19 min, 2.) DMF, 30 min 2: 32 percent / H2O / 8 h / 150 - 160 °C 3: 71 percent / NaH / dimethylformamide / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 1.) NaH / 1.) DMF, 19 min, 2.) DMF, 30 min 2: 32 percent / H2O / 8 h / 150 - 160 °C 3: 71 percent / NaH / dimethylformamide / 1 h 4: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 5: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 6: NaOAc / ethanol / 4 h / Heating 7: 2N HCl / 20 h / Heating 8: 39 percent / pyridine*SO3 / dimethylsulfoxide / 3 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 1.) NaH / 1.) DMF, 19 min, 2.) DMF, 30 min 2: 32 percent / H2O / 8 h / 150 - 160 °C 3: 71 percent / NaH / dimethylformamide / 1 h 4: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 5: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone 6: NaOAc / ethanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1.) NaH / 1.) DMF, 19 min, 2.) DMF, 30 min 2: 32 percent / H2O / 8 h / 150 - 160 °C 3: 71 percent / NaH / dimethylformamide / 1 h 4: H2 / 5percent Pd/C / ethyl acetate / 760 Torr 5: 1.) aq. HBr, NaNO2, 2.) Cu2O / 1.) acetone, 5 deg C, 2.) acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 16h; | 20 A mixture of /V-[(2S)-5-hydroxy-2,3-dihydro-1 H-inden-2-yl]-2-propanesulfonamide (200mg, 0.783 mmol, Description 3) and 1-(6-methyl-3-pyridinyl)ethanol (107 mg, 0.783 mmol, Description 5) in dichloromethane (10 ml) was stirred under argon at room temperature, Triphenylphosphine (205 mg, 0.783 mmol) and diisopropyl azodicarboxylate (0.152 ml, 0.783 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. Solvent was removed by rotary evaporation and the desired product was purified by SCX eluting with 1 M ammonia in methanol solution and MDAP, then concentrated to a small volume. The residual material was partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, filtered and evaporated in vacuo to give the product as free base. The free base was dissolved in methanol and treated with ethereal hydrochloride to give the title compound (121 mg) as a white solid.LC/MS (ES): Found 375 (ES+), retention time 0.70mins (2 minute method). C20H26N2O3S requires 374.1 H-NMR (400MHz, DMSOd6): δ 8.78 (1 H, d, J=1.6Hz), 8.42 (1 H, m), 7.84 (1 H, d, J=8.4Hz), 7.40 (1 H, m), 7.04 (1 H, d, J=8.4Hz), 6.83 (1 H, s), 6.74 (1 H, m), 5.69 (1 H, m), 4.03 (1 H, m), 3.21-3.16 (1 H, m), 3.09-3.01 (2H, m), 2.78-2.70 (2H, m), 2.69 (3H, s) 1.58 (3H, d, J=6.4Hz), 1.22 (6H, d, J=6.8Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C 5.1: piperidine; ethanol / 15 h / Reflux 6.1: hydrogenchloride / water; methanol / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C 5.1: piperidine; ethanol / 15 h / Reflux 6.1: hydrogenchloride / water; methanol / 4 h / Reflux 7.1: triethylamine / dichloromethane; methanol; acetonitrile; hexane; ethanol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C 5.1: piperidine; ethanol / 15 h / Reflux 6.1: hydrogenchloride / water; methanol / 4 h / Reflux 7.1: triethylamine / dichloromethane; methanol; acetonitrile; hexane; ethanol / Resolution of racemate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C 5.1: piperidine; ethanol / 15 h / Reflux 6.1: hydrogenchloride / water; methanol / 4 h / Reflux 7.1: triethylamine / dichloromethane; methanol; acetonitrile; hexane; ethanol / Resolution of racemate 8.1: sodium hydroxide; cobalt(II) chloride hexahydrate; water; sodium tetrahydroborate / tetrahydrofuran; butane-2,3-dione dioxime / 13 h / 10 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: sodium carbonate; ethanol / toluene / 5 h / 85 °C 5.1: piperidine; ethanol / 15 h / Reflux 6.1: hydrogenchloride / water; methanol / 4 h / Reflux 7.1: triethylamine / dichloromethane; methanol; acetonitrile; hexane; ethanol / Resolution of racemate 8.1: sodium hydroxide; cobalt(II) chloride hexahydrate; water; sodium tetrahydroborate / tetrahydrofuran; butane-2,3-dione dioxime / 13 h / 10 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Me2Zn (5.63 mmol, 1 M in toluene, 5.63 ml_) was added to an oven-dried and N2- purged round-bottomed flask and MeMgBr (0.497 mmol, 3 M in ether) was added over 1 min. The solution was stirred at 15 C for 30 min. This solution was added drop wise over 30 mins to a -78 C solution of 2-methyl-N-[(E)-(6-methylpyridin-3- yl)methylidene]propane-2-sulfinamide (Preparation 54, 0.7 g, 3.31 mmol) in anhydrous THF (10 ml_) so as to maintain the internal temperature below -70 C. Upon complete addition the reaction was stirred at -78 C for 1 hr and then allowed to warm to 15 C. The reaction was quenched with sat. aqueous NH4CI solution, the mixture was filtered, and the residue concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with DCM:MeOH (100 :0 to 60 :40) to afford the title compound as a colorless oil, 650 mg, 76% (title compound was isolated in ~3: 1 ratio with 1 -(6-methylpyridin-3-yl)ethanol and was used as is in the next step). 1H NMR (400 MHz, CDCI3): delta 1 .23 (s, 9H), 1 .54 (d, 3H), 2.56 (s, 3H), 4.53-4.60 (m, 1 H), 7.13-7.19 (m, 1 H), 7.60 (dd, 1 H), 8.50 (br s, 1 H). LCMS m/z = 241 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: potassium carbonate / toluene; ethanol / 5 h / 85 °C 5.1: piperidine / ethanol / 15 h / Reflux 6.1: butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate; sodium hydroxide / tetrahydrofuran; water / 12 h / 10 - 20 °C 7.1: hydrogenchloride / ethanol; water / 4 h / Reflux 8.1: d(4)-methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: 5 h / 160 °C / Sealed tube 3.1: triethylamine / dichloromethane / 1 h / 0 °C 4.1: potassium carbonate / toluene; ethanol / 5 h / 85 °C 5.1: piperidine / ethanol / 15 h / Reflux |
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