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CAS No. : | 10165-86-3 | MDL No. : | MFCD08275010 |
Formula : | C8H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BZOWIADSJYMJJJ-UHFFFAOYSA-N |
M.W : | 165.15 | Pubchem ID : | 586269 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.9 |
TPSA : | 56.26 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) : | -6.95 cm/s |
Log Po/w (iLOGP) : | 1.11 |
Log Po/w (XLOGP3) : | 0.5 |
Log Po/w (WLOGP) : | 0.68 |
Log Po/w (MLOGP) : | -0.28 |
Log Po/w (SILICOS-IT) : | 1.35 |
Consensus Log Po/w : | 0.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.35 |
Solubility : | 7.36 mg/ml ; 0.0446 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.25 |
Solubility : | 9.25 mg/ml ; 0.056 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.04 |
Solubility : | 1.5 mg/ml ; 0.0091 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
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 |
---|---|---|
97% | With manganese(IV) oxide In dichloromethane at 20℃; for 4 h; | A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g , 37 mmol) and Mn02 (32,3 g , 372 mmol) in DCM ( 200 mL ) was stirred at 20 °C for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5/1) to afford methyl 6-formylnicotinate (6 g , 97percent).MS-ESI (m/z): 166.2 (M+l) + (LC-MS method C; Ret. time: 0.36 min). |
97% | With manganese(IV) oxide In dichloromethane at 20℃; for 4 h; | (c) methyl 6-formylnicotinate A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g, 37 mmol) and MnO2 (32.3 g, 372 mmol) in DCM (200 mL) was stirred at 20° C. for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc=5/1) to afford methyl 6-formylnicotinate (6 g, 97percent). MS-ESI (m/z): 166.2 (M+1)+ (LC-MS method C; Ret. time: 0.36 min). |
86% | With Dess-Martin periodane In dichloromethane at 20℃; Inert atmosphere | Dess-Martin periodinane (3.0 g, 7.2 mmol) was added slowly to the mixture of compound 38 (1.0 g,6.0 mmol) in DCM (10 mL). The resulting mixture continued to stir at room temperature overnight.The reaction was quenched with water. The aqueous phase was extracted with EtOAc. The combinedorganic phases were then processed in the usual way and chromatographed (3:1 petroleum ether/EtOAc)to yield compound 39 (0.85 g, 86percent). |
85.6% | With Dess-Martin periodane In dichloromethane | The A solution of compound 25 (1.0 g, 6. Ommol)Dissolved in dichloromethane (10 mL)in,Add a Dess-Martin periodinane(3.0 g, 7.2 mmo 1)TLC to track the degree of completion of the assay,After the reaction is completed,Water extraction, ethyl acetate extraction,Concentration gave compound 26 (0.6 g, 85.6percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With iodine; trifluoroacetic acid In dimethyl sulfoxide at 160℃; for 2 h; | A mixture of methyl 6-methylnicotinate (5.0 g, 33.0 mmol), 12 (8.4 g, 33.2 mmol) andTFA (7.5 mL, 11.5 g, 0.1 mol) in DMSO (100 mL) was heated to 160°C for 2 h. Themixture was allowed to cool to RT and poured into a 1 N solution ofNa2S2O3 (aq.) (0.5L) solution, made alkaline using NaOH (2 N) and extracted with EtOAc (3 x 0.2 L).The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in DCM and applied on a short pad of silica. The product was eluted with EtOAc to afford the product as a yellowish solid (3.8 g, 23 mmol, 70percent). |
46% | Stage #1: With iodine; tert-Butyl iodide; trifluoroacetic acid In dimethyl sulfoxide at 160℃; for 3 h; Stage #2: With sodium thiosulfate In water; dimethyl sulfoxide Stage #3: With sodium hydrogencarbonate In water; dimethyl sulfoxide |
A solution of 6-methyl nicotinic acid methyl ester (1.00 g, 6.62 mmol), iodine (1.68 g, 6.62 mmol), 2-iodo-2-methylpropane (0.478.g, 2.60 mmol) and trifluoroacetic acid (2.26 g, 19.8 mmol) in anhydrous DMSO was heated for 3 h at 160° C. The reaction mixture was cooled to room temperature (rt) and treated with 1 N aq. Na2S2O3 (50 mL). The reaction mixture was adjusted to pH 10 with 1 N aq. NaHCO3. The reaction mixture was extracted with ethyl acetate (3*100 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. Chromatography of the residue (SiO2; 0-3percent EtOH:DCM) gave the title compound as a solid (0.506 g, 46percent). |
37% | With iodine; trifluoroacetic acid In dimethyl sulfoxide at 0 - 140℃; for 3.5 h; | Iodine (33.5g, 0.13mmol) and trifluoroacetic acid (35.3ml, 0.4mmol) were added to a solution of methyl 6-carboxylate-1-picoline (20g, 0.13mol) in N,N-dimethylsulfoxide (200ml) at 0°C and the mixture was stirred for 1 hourand then heated to 140°C and stirred for 2.5 hours. After being cooled to 0°C, the reaction was quenched with saturatedsodium thiosulfate solution (30ml) and stirred for 30 minutes. The aqueous layer was extracted with ethyl acetate (150ml3 3) and the organic layers were combined and washed with brine (50ml 3 2), dried over anhydrous sodium sulfate,filtered, concentrated in vacuo and the residue was purified by flash silica gel column chromatography to give the titlecompound (8g, yield 37percent). 1H NMR (400MHz, CHLOROFORM-d) ppm :10.14 (s, 1H), 9.36 (s, 1H), 8.47 (dd, J=1.3, 8.0Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 4.05 - 3.94 (s, 3H). |
15% | With selenium(IV) oxide In 1,4-dioxane at 85℃; Inert atmosphere | 250mL single-neck flask was added methyl 6-methylpyridine-3-carboxylate (10g, 66.15mmol) and 1,4-dioxane (100mL), was added under stirring selenium dioxide (14.7g, 132mmol), nitrogen heated to 85 under the protection of the reaction overnight. Cooling to room temperature, filtered, and the solvent was removed by rotary evaporation, the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1), give a pale yellow solid 1.6g, Yield: 15percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With Dess-Martin periodane In dichloromethane at 0℃; for 6 h; | 10314] Dimethyl-2,5-pyridinedicarboxylate (960 mg, 4.9mmoles) and CaC12 (2.198 g, 19.7 mmoles) were added to a dried flask. THF (11 mE) and EtOH (12 mE) were added, and the resulting suspension was stirred on ice for 30 minutes. NaI3H4 (465 mg, 12.3 mmoles) was added portion wise with stirring. The reaction was allowed to come to room temperature overnight. Afier 18 h, the reaction was quenched by the dropwise addition of an aqueous solution of NH4C1 (saturated aqueous NH4C1 [20 mE] plus H20 [40 mE]) while stirring on ice. The aqueous layer was extracted with DCM (4x30 mE) and the combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the crude alcohol (678 mg) as a pale yellow solid. The crude alcohol was dissolved in dry DCM (45 mE), after which Dess-Martin periodinane (2.6 g, 6.1 mmoles) was added portion wise while stirring on ice. After 6 h, the reaction was quenched by the dropwise addition of a solution of 5percent Na2S2O3 in half saturated NaHCO3 (80 mE). The aqueous layer was extracted with DCM (3x40 mE). The combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the title compound (504 mg, 62percent) as a pale yellow solid. ‘H NMR (400 MHz, CDC13) ö 10.16 (s, 1H), 9.38 (dd, J=0.5, 2.0 Hz, 1H), 8.49 (dd, J=2.0, 8.0 Hz, 1H), 8.05 (dd, J=0.5, 8.0 Hz, 1H), 4.02 (s, 1H); ‘3C NMR (100 MHz, CDC13) ö 192.6, 164.8, 154.9, 151.2, 138.3, 121.1, 52.9; HRMS (El) mlz 165.0415 [calc’d for C8H7N03 (M) 165.042 1] |
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