Structure of 37669-78-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 37669-78-6 |
Formula : | C10H13NO2 |
M.W : | 179.22 |
SMILES Code : | O=C(OCC)C1=C(C)N=CC=C1C |
MDL No. : | MFCD00051962 |
InChI Key : | DIZHKKYVLBSXAW-UHFFFAOYSA-N |
Pubchem ID : | 736245 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 50.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
39.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.26 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.28 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.47 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.25 |
Solubility | 0.999 mg/ml ; 0.00557 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.28 |
Solubility | 0.933 mg/ml ; 0.00521 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.28 |
Solubility | 0.0943 mg/ml ; 0.000526 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.09 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.74 |
* 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 |
---|---|---|
99% | A mixture of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (3.58 g, 20 mmol) and an aqueous solution of NaOH (10M, 20 ml) in ethanol (20 ml) was stirred at room temperature for 24 hours. The mixture was cooled to 0 C. and methanol (200 ml) was added follow by aqueous HCl (10 M) to adjust pH to 7. The resulting precipitated (NaCl) was filtered off.The filtrated was concentrated to remain approximately 20 ml and methanol (100 ml) was added again to precipitate the remaining sodium chloride. The precipitation (NaCl) was repeated until all NaCl was removed from methanolic solution of the reaction mixture. The mixture was concentrated to dryness to yield 1a (3.01 g, 19.9 mmol, 99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (2 g, 11.2 mmol) in anhydrous THF (10 mL), previously cooled to -10C, was added 2.4M lithium aluminium hydride (9.3 mL, 22.4 mmol) portionwise. Stirring was continued for 16 h. Water (0.8 mL) was added dropwise, followed by 15% aqueous sodium hydroxide solution (0.8 mL), then more water (2.4 mL). The reaction mixture was stirred at r.t. for 1 h, then extracted with DCM (2 x 100 mL). The organic phases were combined, dried over Na2S04 and filtered. The solvent was removed in vacuo to give the title compound (1.53 g, 100%) as a white solid. Method B HPLC-MS: MH+ mlz 138, RT 0.26 minutes | |
87.53% | With lithium aluminium tetrahydride; In tetrahydrofuran; at -30 - -10℃; for 3h;Inert atmosphere; | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (1 g, 5.58 mmol, 1 equiv.) in THF (40 mL) was batch added LiAlH4(317.7 mg, 8.37 mmol, 1.50 equiv.) at -30 degrees Celsius under nitrogen atmosphere. The resulting mixture was stirred for 3h at -30 degrees Celsius~ -10 degrees Celsius. The desired product could be detected by LCMS and TLC. The reaction mixture was quenched with water(0.5mL) at -30 degrees Celsius and quenched with 15% NaOH(aq). The mixture was filtrated, the filtrate was concentrated under reduced pressure to crude product. The crude product was purified by Prep-TLC (PE / EA 1:1) to afford (2,4-dimethylpyridin-3- yl)methanol (670 mg, 87.53%) as a white solid. |
84.9% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (1.0 g, 5.57 mmol) in dry tetrahydrofuran (10 mL), lithium alu minum hydride (1.0 M solution in THF, 8.36 mL, 8.36 mmol) was added at 0C during 30 minutes and stirred at rt for 1.5h. After 1.5 h, excess of LiA1H4 was decomposed with crushed ice and the residue was extracted with ethyl acetate (300 mL). The combined organic layers were dried over Na2SO4 and concentrated and the product was purified by silica gel column chromatography (2.5% MeOH: dichloromethane) to provide the title compound (0.650 g, 84.9%), 1H (400 MHz, DMSO-d6) delta ppm 8.16-8.18 (d, 1H), 7.01-7.02 (d, 1H), 4.89-4.92, (t, 1H), 4.50-4.51 (d, 2H), 2.50 (s, 3H), 2.34 (s, 3H). |
67% | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (5.35 g, 30 mmol) in DCM (150 mL) under argon at -78 0C was added diisobutylaluminium hydride (IM in hexane, 100 mL, 100 mmol). The reaction mixture was stirred for 24 hours and then added to a saturated aqueous solution of Rochelle salt (200 mL) at 0 0C. The mixture was stirred until two layers had formed. The phases were separated and the aqueous phase was extracted with DCM (2 x 150 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The residue was recrystallised from EtOAc to give (2,4-dimethyl- pyridin-3-yl)-methanol (2.76 g, 67%) as a pale yellow solid. Analytical LCMS: (System A, Rtau = 0.46 min), ES+: 138.0 [MH]+. | |
54.8% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; | To a stirred solution of2,4-Dimethyl-nicotinic acid ethyl ester (6) (500 mg, 2.79 mmol) in THF (10 mL) was cooled to 0C and LiAlH4 (424 mg, 11.159 mmol) was added and the resultant reaction was stirred at Rt for 2 hour. The reaction was quenched with 2N NaOH solution and stirred for 10 min. The reaction mixture was then filtered off and washed with ethyl acetate. The filtrate was then further washed with brine, dried over sodlium sulfate and concentrated to afford Intermediate 7 (210 mg, 54.8%) as yellow gum. |
Example 31 : 4-Chloro-N-[5-chloro-2-(2,4-dimethyl-pyridine-3-carbonyl)-Pyridin-3- yl]-3-trifluoromethyl-benzenesulfonamide; [00416] Step 1 : A solution of lithium aluminum hydride in THF (1.0 M, 40 mL, 40 mmol) placed in a 100-mL round bottom flask equipped with a magnetic stirring bar was cooled in an ice bath and cautiously treated with a solution of <strong>[37669-78-6]2,4-dimethyl-nicotinic acid ethyl ester</strong> (5.4 g, 30 mmol) in anhydrous THF (10 mL) over 5 min period. After the addition was complete the cold bath was removed and the mixture was allowed to stir at room temperature for 2 h. The reaction mixture was then cooled in an ice bath and the excess LAH was quenched by drop wise addition of water until gas evolution stopped. The reaction mixture was then basified with 2M NaOH to pH 9-10. Ether (100 mL) was added the mixture was washed with 1 M NaOH, water and brine. The organic layer was EPO <DP n="112"/>dried over MgSO4 and the solvent was evaporated to yield (2,4-dimethyl-pyridin- 3-yl)-methanol as a white solid. MS: (M+H) /z = 138. | ||
With sodium hydroxide; In tetrahydrofuran; water; | Step 1: Preparation of 3-hydroxymethyl-2,4-dimethylpyridine To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (3.00 g) in tetrahydrofuran (30 mL), lithium aluminum hydride (1.21 g) was added portionwise with ice-bath cooling. After stirring for 2 hours, water (1.2 mL), 15% aqueous sodium hydroxide (1.2 mL) and water (3.6 mL) were successively added to the resulting reaction mixture and the mixture was stirred at room temperature. The organic layer was obtained, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (2.26 g) as white crystals. | |
With diisobutylaluminium hydride; In dichloromethane; at -70℃; for 2h; | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (538 mg, 3 mmol) in DCM (5 ml) was added dropwise, at -70C, DIBAL-H 1 M in DCM (8 ml, 8 mmol). The reaction mixture was stirred at this temperature during 2 h. The reaction mixture was quenched by a slow addition of EtOAc (1 ml) and H20 (1 ml), then concentrated. The crude residue was purified by flash chromatography on silica gel (gradient EtOAc then DCM/MeOH 95/5 to 9/1 ). TLC, Rf (DCM/MeOH 9/1 ) = 0.22; [M+H]+ = 138.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 48h; | To a solution of <strong>[37669-78-6]2,4-dimethyl-nicotinic acid ethyl ester</strong> (1.79 g, 10.0 mmol) in CH2Cl2 (50 mL) was added 3-chloroperoxybenzoic acid (77% max., 4.48 g, 20.0 mmol). The mixture was stirred at room temperature for 2 days, and then concentrated under reduced pressure. The residual solid was purified by flash column chromatography on silica gel (EtOAc) to afford 2,4-dimethyl-1-oxy-nicotinic acid ethyl ester as a white solid (1.95 g, 100%). 1H NMR (CDCl3) delta 1.41 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 2.49 (s, 3H), 4.44 (q, 2H, J=7.2 Hz), 7.00 (d, 1H, J=6.6 Hz), 8.19 (d, 1H, J=6.6 Hz). |
With dihydrogen peroxide; In dichloromethane; acetic acid; | Preparation of 2,4-dimethyl-1-oxy-nicotinic acid ethyl ester: To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (2.0 g, 11.2 mmol) in AcOH (28 mL) was added H2O2 (34-37%, 1.1 mL, 11.2 mmol) and the resultant mixture was heated to 70 C. for 3 hours. A second aliquot of H2O2 (34-37%, 1.1 mL, 11.2 mmol) was added and the mixture heated at 70 C. overnight. The reaction mixture was concentrated under reduced pressure and the resulting syrup was dissolved in CH2Cl2 (150 mL) and washed with saturated NaHCO3 (2*25 mL). The aqueous layer was extracted with CH2Cl2 (2*100 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford the desired N-oxide (2.07 g, 95%/o). 1H NMR (CDCl3) delta 1.41 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 2.49 (s, 3H), 4.44 (q, 2H, J=7.2 Hz), 6.99 (d, 1H, J=6.6 Hz), 8.19 (d, 1H, J=6.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | Step 2. The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0 C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0 C. and quenched with EtOAc (2.5 mL), then H2 O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2 O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (0.59 g, 3.29 mmol) and cyclopropane carboxylic acid (1.2 ml (15.1 mmol) in 10% aqueous H2SO4 (3 ml) was added AgNO3 (154 mg, 0.91 mmol) followed by a solution of ammonium persulfate (1.541 g, 6.75 mmol) in water (6 ml) and the mixture stirred at room temperature overnight. The reaction was neutralized to pH 10 with saturated aqueous NH4OH (5 ml) and extracted with EtOAc (3 x 20 ml). The combined organic extracts were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 96:4 then 1:1 then 0:100) to afford desired 6-cyclopropyl-<strong>[37669-78-6]2,4-dimethyl-nicotinic acid ethyl ester</strong> (133 mg, 18%) as a clear oil along with recovered starting <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (0.31 g). 1H NMR (CDCl3) delta 0.93-0.97 (m, 4H), 1.38 (t, 3H, J= 6 Hz), 1.92-2.02 (m, IH), 2.28 (s, 3H), 2.47 (s, 3H), 4.39 (q, 2H, J= 6 Hz), 6.73 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | A 25 mL 3-neck flask equipped with stir bar, addition funnel, N2 inlet tube and reflux condenser was charged with 4a (l.Og, 4.94 mmol) and (dry) toluene (4 mL) and cooled to 0 C. Trimethylaluminum (2.5 mL of a 2.0 M toluene solutionn, 5.0 mmol) was added dropwise, then allowed to warm to RT. 2,4-Dimethyl-nicotinic acid ethyl ester (80, 0.93 g, 5.2 mmol) in toluene (1 mL) was added dropwise then heated at 120 C for 18 h. The reaction mixture was cooled in an ice bath and MeOH (2 mL) was added. The mixture was brought to RT, heated at reflux for 10 min then recooled to RT. The mixture was filtered through a CELITE pad. The filtrate was washed with brine, dried (MgS04) then concentrated in vacuo. The crude product was purified by flash chromatography on silica eluting with 7.5% MeOH (containing 2% NH40H) / DCM to afford 1.17 g, (71%) of 81 as a pale yellow liquid: ms (ES+) m/z 336 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To the solution of ethyl 2,4-dichloropyridine-3-carboxylate (3.3 g, 15 mmol) in dioxane (100 niL) in a 500 mL round bottom flask was added dimethylzinc (22 mL, 1.0 M in hexane) and (l,l'-bis(diphenylphosphino)ferrocene) dichloropalladium (II) dichloromethane complex (300 mg, 0.4 mmol). The resulting mixture was heated at 700C for 8 hours. After cooling, the reaction was quenched by addition of methanol (1OmL). The mixture was poured into water (500 mL) and extracted with dichloromethane (3 x 200 mL). The combined organic layer was evaporated, and the crude residue was filtered through a silica pad (5 cm) with 20% ethyl acetate in hexane (200 mL). After evaporation, the oily ethyl 2,4-dimethylpyridine-3- carboxylate was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With trichloroisocyanuric acid; In dichloromethane; at 20℃; | Synthesis of ethyl 2-(chloromethyl)-4-methylnicotinate (3) To a stirred solution of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (1, 10 g, 0.055 mol) in dichloromethane (200 mL), 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (2, 19.35 g, 0.083 mol) was added. The reaction was stirred at room temperature overnight. After completion, the reaction mixture was concentrated and quenched with saturated aqueous solution of sodium carbonate till pH 8. The mixture was extracted with dichloromethane (2*150 mL). The organics were combined, dried over magnesium sulfate, filtered and concentrated to afford ethyl 2-(chloromethyl)-4-methylnicotinate (2) as a yellow oil. Yield: 10.0 g, 84%; MS (ESI) m/z 214.2 [M+1]+. |
With trichloroisocyanuric acid; In dichloromethane; at 20 - 25℃; for 18h;Inert atmosphere; | As shown in step 1-i of Scheme 1, to a solution of ethyl 2,4- dimethylpyridine-3-carboxylate (Compound 1001, 20.2 g, 112.5 mmol) in dichloromethane (100 mL) under an atmosphere of nitrogen was added portionwise 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (31.4 g, 135.0 mmol) over 15 minutes. The reaction mixture was stirred at room temperature for 18 hours. The resulting white precipitate was filtered and the filtrate was then washed sequentially with aqueous saturated NaHCO3 solution (2 x 100 mL) and brine (100 mL). The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to afford ethyl 2- (chloromethyl)-4-methylnicotinate (22.9 g, Compound 1002) as a yellow oil: ESMS (M-?-H)=21 3.96. This material was used in the next step without further purification: |
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