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CAS No. : | 179555-11-4 | MDL No. : | MFCD09835242 |
Formula : | C7H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FBKFFOOSODQYPO-UHFFFAOYSA-N |
M.W : | 152.15 | Pubchem ID : | 9964149 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 40.57 |
TPSA : | 76.21 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.94 cm/s |
Log Po/w (iLOGP) : | 0.77 |
Log Po/w (XLOGP3) : | 0.4 |
Log Po/w (WLOGP) : | 0.68 |
Log Po/w (MLOGP) : | -0.96 |
Log Po/w (SILICOS-IT) : | 0.46 |
Consensus Log Po/w : | 0.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.37 |
Solubility : | 6.45 mg/ml ; 0.0424 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.57 |
Solubility : | 4.13 mg/ml ; 0.0271 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.41 |
Solubility : | 5.92 mg/ml ; 0.0389 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
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 |
---|---|---|
88 mg (81%) | In benzyl alcohol | 1.12 EXAMPLE 44 STR46 2-Amino-5-methoxycarbonyl-4-methylpyridine EXAMPLE 44 STR46 2-Amino-5-methoxycarbonyl-4-methylpyridine A mixture of 2-amino-5-carboxy-4-methylpyridine (100 mg, 0.657 mmol) in 7:3 benzene-methanol (4 mL) was treated with (trimethylsilyl)diazomethane (2M solution in hexanes, 0.33 mL, 0.66 mmol). The mixture was evaporated and the residue chromatographed on silica gel eluding with 25% acetone/hexane to afford pure title compound; yield 88 mg (81%). 1 H NMR (400 MHz, CD3 OD): δ 2.47 (s, 3H), 3.80 (s, 3H), 6.39 (s, 1H), 8.48 (s, 1H). Mass spectrum (FAB): m/e=167 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | 6-Amino-4-methyl-nicotinonitrile (1.7 g, 12.8 mmol) was suspended in 4N sodium hydroxid solution and stirred 5 h at 100C to obtain a clear solution. The reaction mixture was cooled in an icebath and acidified by addition of 4N hydrochloric acid. The precipitate was filtered and washed with little water. The residue was dissolved in MeOH, the solvent evaporated at reduced pressure and the product dried at high vacuum to yield the title compound 1.74 g (90%) as colorless solid. [1 H-NMR (DMSO, 600 MHz) 12.17 (s, 1 H), 8.45 (s, 1 H), 6.56 (2H), 6.23 (s, 1 H), 2.38 (s, 3H); LCMS RtD = 1.910 min; [M+H]+ = 153.0]. | |
134 mg (20%) | With sodium hydroxide; In ethanol; | EXAMPLE 43 STR45 2-Amino-5-carboxy-4-methylpyridine A solution of <strong>[179555-10-3]2-amino-5-cyano-4-methylpyridine</strong> (600 mg, 4.50 mmol) in ethanol (7.5 mL) was treated with 10N sodium hydroxide (7.5 mL) for 24 h at reflux temperature. The mixture was cooled and diluted with water (30 mL). The pH was adjusted to 7 with conc. hydrochloric acid and 1N hydrochloric acid. The resulting solid was filtered, dried by suction, washed with ether, and dried in vacuo; yield 134 mg (20%). 1 H NMR (400 MHz, DMSO-d6): delta 2.38 (s, 3H), 6.22 (s, 1H), 8.43 (s, 1H). Mass spectrum (FAB): m/e=153 (M+1). |
With sodium hydroxide; In ethanol; for 24h;Inert atmosphere; Schlenk technique; Reflux; | A mixture of 2-amino-5-bromo-4-methylpyridine (2.0 g, 10.7 mmol) and CuCN (1.1 g, 12.3 mmol) in DMF (2.5 mL) wasrefluxed for 4 h. After the mixture was cooled to room temperature, NaCN (2.15 g) and H2O (6.5mL) were added, and the mixture was stirred and extracted by AcOEt. The solution was washedby aq. 10% CuCN and brine. After the solvent was removed under vacuo, the residue waschromatographed on silica gel (AcOEt/hexane = 1 : 1) to give <strong>[179555-10-3]2-amino-5-cyano-4-methylpyridine</strong> (829 mg, 58%). A solution of <strong>[179555-10-3]2-amino-5-cyano-4-methylpyridine</strong> (706 mg, 5.3mmol) in EtOH (8.8 mL) and aq. 10N NaOH (8.8 mL) was refluxed for 24 h. After cooled toroom temperature, the mixture was diluted by adding H2O (35 mL), neutralized by aq. HCl, and filtered. The solid was washed by ether and H2O to give 6-amino-4-methylpicolinic acidcontaining NaCl (879 mg), which was dissolved in MeOH (16 mL). To this mixture was addedSOCl2 (0.7 mL, 6.7 mmol) and the mixture was refluxed for 20 h. After cooled to roomtemperature, the solvent was removed under vacuo. To the residue H2O (20 mL) was added andpH was adjusted to 13 by aq. 1N NaOH and filtered. The solid was washed by H2O and driedunder vacuo to give 2-amino-5-methoxycarbonyl-4-methylpyridine (484 mg), which wasdissolved in aq 15% H2SO4 (10.4 mL). To the solution was added NaNO2 (402 mg, 5.81 mmol)at 0 C and the mixture was stirred for 2 h at 0 C and, then, 2 h at room temperature. Themixture was extracted by AcOEt and the solvent was removed under vacuo. The residue waschromatographed on silica gel (AcOEt) to give 2bd (105 mg, 21%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dichlorosulfoxide Reflux; Inert atmosphere; | |
40% | Stage #1: methanol; 2-amino-4-methyl-5-pyridinecarboxylic acid With sulfuric acid at 85℃; Stage #2: With Sodium hydrogenocarbonate In methanol; ethyl acetate | A2.c -Amino-4-methyl-nicotinic acid methyl ester6-Amino-4-methyl-nicotinic acid (1.7 g, 11.2 mmol) was dissolved in MeOH (23 ml) and cone, sulfuric acid (0.30 ml, 5.6 mmol) was added dropwise. The reaction was heated (bath temperature 85°C) over night. Then, the mixture was diluted with EtOAc, washed with NaHC03- and NaCI-soln., dried (Na2S0 ), filtered and concentrated. The residue was crystallized from DCM(MeOH)/diethylether/hexane to give the title compound as yellowish crystals (735 mg, 40%). [1 H-NMR (DMSO, 600 MHz) 8.46 (s, 1 H), 6.65 (2H), 6.25 (s, 1 H), 3.73 (s, 3H), 2.37 (s, 3H); LCMS RtD = 2.355 min; [M+H]* = 167.0]. |
484 mg | With dichlorosulfoxide for 20h; Inert atmosphere; Schlenk technique; Reflux; | 5-Methoxycarbonyl-4-methyl-2-hydroxypyridine (2bd) A mixture of 2-amino-5-bromo-4-methylpyridine (2.0 g, 10.7 mmol) and CuCN (1.1 g, 12.3 mmol) in DMF (2.5 mL) wasrefluxed for 4 h. After the mixture was cooled to room temperature, NaCN (2.15 g) and H2O (6.5mL) were added, and the mixture was stirred and extracted by AcOEt. The solution was washedby aq. 10% CuCN and brine. After the solvent was removed under vacuo, the residue waschromatographed on silica gel (AcOEt/hexane = 1 : 1) to give 2-amino-5-cyano-4-methylpyridine (829 mg, 58%). A solution of 2-amino-5-cyano-4-methylpyridine (706 mg, 5.3mmol) in EtOH (8.8 mL) and aq. 10N NaOH (8.8 mL) was refluxed for 24 h. After cooled toroom temperature, the mixture was diluted by adding H2O (35 mL), neutralized by aq. HCl, and filtered. The solid was washed by ether and H2O to give 6-amino-4-methylpicolinic acidcontaining NaCl (879 mg), which was dissolved in MeOH (16 mL). To this mixture was addedSOCl2 (0.7 mL, 6.7 mmol) and the mixture was refluxed for 20 h. After cooled to roomtemperature, the solvent was removed under vacuo. To the residue H2O (20 mL) was added andpH was adjusted to 13 by aq. 1N NaOH and filtered. The solid was washed by H2O and driedunder vacuo to give 2-amino-5-methoxycarbonyl-4-methylpyridine (484 mg), which wasdissolved in aq 15% H2SO4 (10.4 mL). To the solution was added NaNO2 (402 mg, 5.81 mmol)at 0 °C and the mixture was stirred for 2 h at 0 °C and, then, 2 h at room temperature. Themixture was extracted by AcOEt and the solvent was removed under vacuo. The residue waschromatographed on silica gel (AcOEt) to give 2bd (105 mg, 21%): |
With dichlorosulfoxide for 16h; Reflux; | 26 Reference Example 26: Preparation of Intermediate I-26 Thionyl chloride (15 mL) was added to a solution of Intermediate 1-25 (7.8 g, 51.3 mmol) in methanol (80 mL) at room temperature. The reaction mixture was refluxed for 16 hours. Cool to room temperature, remove most of the methanol solvent under reduced pressure, add water (100 mL) to dilute, and adjust pH to 13 with aqueous sodium hydroxide solution (2mol/L), separate out solids, filter with suction, wash the filter cake with water, and dry to obtain an intermediate I-26. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: ISOPROPYLAMIDE / 24 h / 170 °C / Inert atmosphere 1.2: 0.25 h 2.1: sodium hydroxide / lithium hydroxide monohydrate / 5 h / 100 °C 2.2: Cooling with ice | ||
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 4 h / Inert atmosphere; Schlenk technique; Reflux 2: sodium hydroxide / ethanol / 24 h / Inert atmosphere; Schlenk technique; Reflux | ||
Multi-step reaction with 2 steps 1.1: N,N-dimethyl acetamide / 16 h / 170 °C / Inert atmosphere 1.2: 0.25 h / 0 °C 2.1: sodium hydroxide / lithium hydroxide monohydrate / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sulfuric acid / 85 °C 2: sodium hydrogencarbonate / ethanol; water / 1.5 h / 90 °C 3: sodium hydroxide; water / methanol / 3 h / 20 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 85 °C 2: sodium hydrogencarbonate / ethanol; water / 1.5 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-amino-4-methyl-5-pyridinecarboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: ethanamine hydrochloride In N,N-dimethyl-formamide | Intermediate 5O. N-ethyl-4-methyl-pyridine-3-carboxamide 2-Amino-4-methyl-5-pyridinecarboxylic acid (CAS 179555-1 1-4, 250 mg, 1.64 mmol, 1.0 equiv.) was mixed with HATU (686 mg, 1.80 mmol, 1.1 eq), DIPEA (857 jiL, 4.92 mmol, 3.0 eq) and DMF (1.0 M). The mixture was stirred for 5 minutes at room temperature, EtNH3C1 (201 mg, 2.5 mmol, 1.5 eq) was added and stirring was continued overnight. Next, the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3x10 mL). The combined organic extracts were washed with brine (10 mL), saturated aquaeous NaHCO3 solution (10 mL) and brine again (10 mL). Next, the organic layer was dried and evaporated in vacuo to afford the desired product which was used as such in the next step. LCMS: mlz= 180 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 1 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 70 °C 4: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 °C 5: pyridine / 16 h / 20 °C 6: ammonium hydroxide; iodine / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 3 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / methanol / 0.5 h / 70 °C 4: oxalyl dichloride / N,N-dimethyl acetamide; dichloromethane / 0.5 h / 0 °C 5: pyridine / 3 h / 20 °C 6: ammonium hydroxide; iodine / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: dichlorosulfoxide / 16 h / Reflux 2.1: pyridine / 3 h / 20 °C 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / 0.5 h / 70 °C 4.1: oxalyl dichloride / N,N-dimethyl acetamide; dichloromethane / 0.5 h / 0 °C 5.1: pyridine / 3 h / 20 °C 6.1: NBS / tetrahydrofuran; lithium hydroxide monohydrate / 16 h / 20 °C 6.2: 2 h / 20 °C 7.1: potassium-t-butoxide; trimethyl-oxo-sulfonium iodide / dimethyl sulfoxide / 0.17 h / 20 °C 7.2: 16 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 1 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 1 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 70 °C 4: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 1 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 70 °C 4: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 °C 5: pyridine / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 3 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / methanol / 0.5 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 3 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / methanol / 0.5 h / 70 °C 4: oxalyl dichloride / N,N-dimethyl acetamide; dichloromethane / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: dichlorosulfoxide / 16 h / Reflux 2: pyridine / 3 h / 20 °C 3: sodium hydroxide; lithium hydroxide monohydrate / methanol / 0.5 h / 70 °C 4: oxalyl dichloride / N,N-dimethyl acetamide; dichloromethane / 0.5 h / 0 °C 5: pyridine / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: dichlorosulfoxide / 16 h / Reflux 2.1: pyridine / 3 h / 20 °C 3.1: sodium hydroxide; lithium hydroxide monohydrate / methanol / 0.5 h / 70 °C 4.1: oxalyl dichloride / N,N-dimethyl acetamide; dichloromethane / 0.5 h / 0 °C 5.1: pyridine / 3 h / 20 °C 6.1: NBS / tetrahydrofuran; lithium hydroxide monohydrate / 16 h / 20 °C 6.2: 2 h / 20 °C |
[ 94015-05-1 ]
4-Methylnicotinic acid hydrochloride
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[ 94015-05-1 ]
4-Methylnicotinic acid hydrochloride
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