Structure of 100189-17-1
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 100189-17-1 |
Formula : | C8H11NO |
M.W : | 137.18 |
SMILES Code : | OCCC1=CC=C(C)N=C1 |
MDL No. : | MFCD09926432 |
InChI Key : | CRZJKFRQNPDUIV-UHFFFAOYSA-N |
Pubchem ID : | 13566816 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.14 |
TPSA ? Topological Polar Surface Area: Calculated from |
33.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.66 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.92 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.96 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.53 |
Solubility | 4.09 mg/ml ; 0.0298 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.11 |
Solubility | 10.7 mg/ml ; 0.078 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.62 |
Solubility | 0.332 mg/ml ; 0.00242 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) |
No |
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 |
-6.55 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) |
1.47 |
* 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 dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 1.0h; | To a stirred solution of 2-(6-methylpyridin-3-yl) acetic acid (1 .5g, 9.9 mmol) in dry THF(20 mL) was added Borane-DMS (2 mL, 19.8 mmol) drop wise at 0 00. The reactionmixture was stirred at RT for lh. Reaction completion was monitored by TLC. Reactionmixture was quenched with methanol at 0 00 The reaction mixture was concentratedcompletely and extracted with ethyl acetate, washed with water (2 x 10 mL), sodium bicarbonate (2 x 10 mL) and brine solution (2 x 10 mL). Combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated and the crude mass obtained was purified by flash column chromatography to get the title product as pale yellow liquid. 1HNMR (400 MHz, DMSO-d6): 6 8.55 (s, 1H), 7.93 (dd, J = 8.0, 1.9 Hz, 1H), 7.56 (d, J =8.0 Hz, 1H), 4.74 (s, 1H), 3.65-3.60 (m, 2H), 2.77 (t, J = 6.2 Hz, 2H), 2.59 (s, 3H).LCMS: (Method B) 138.2 (M+H), Rt. 3.5 mm, 91.6% (Max). | |
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 1.0h; | Step 3: 2-(6-methylpyridin-3-yl) ethan-1-ol To a stirred solution of 2-(6-methylpyridin-3-yl) acetic acid (1.5g, 9.9 mmol) in dry THF (20 mL) was added Borane-DMS (2 mL, 19.8 mmol) drop wise at 0 C. The reaction mixture was stirred at RT for 1 h. Reaction completion was monitored by TLC. Reaction mixture was quenched with methanol at 0 C. The reaction mixture was concentrated completely and extracted with ethyl acetate, washed with water (2 * 10 mL), sodium bicarbonate (2 * 10 mL) and brine solution (2 * 10 mL). Combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated and the crude mass obtained was purified by flash column chromatography to get the title product as pale yellow liquid. 1H NMR (400 MHz, DMSO-d6): delta 8.55 (s, 1 H), 7.93 (dd, J = 8.0, 1.9 Hz, 1 H), 7.56 (d, J = 8.0 Hz, 1 H), 4.74 (s, 1 H), 3.65-3.60 (m, 2H), 2.77 (t, J = 6.2 Hz, 2H), 2.59 (s, 3H). LCMS: (Method B) 138.2 (M+H)+, Rt. 3.5 min, 91.6% (Max). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With triethylamine; In dichloromethane; at 0 - 20℃; for 1.0h; | To a stirred solution of <strong>[100189-17-1]2-(6-methylpyridin-3-yl)ethan-1-ol</strong> (0.5 g, 3.6 mmol) in dry DCM(10 mL) at 0 00 was added triethyl amine (1.5 mL, 10.8 mmol, Spectrochem) followed byaddition of methane sulfonyl chloride (0.4 mL, 5.4 mmol, Spectrochem). Reaction mass was brought to RT and stirred for 1 h. Reaction completion was monitored by TLC. Reaction mass was diluted with DCM, washed with water, dried over Na2SO4 and evaporated. The crude was isolated as pale brown liquid and was taken for next stepwithout any further purification (0.36 g, 46%). 1H NMR (400 MHz, DMSO-d6): 6 8.63 (s,1H), 8.00 (dd, J = 8.0, 1.8 Hz, 1H), 7.62-7.58 (m, 1H), 4.45 (t, J = 6.4 Hz, 2H), 3.14 (s,3H), 3.07 (d, J = 6.4 Hz, 2H), 2.59 (s, 3H). LCMS: (Method A) 216.0 (M+H), Rt. 3.3 mm,50.2% (Max). |
46% | With triethylamine; In dichloromethane; at 0 - 20℃; | Step 4: 2-(6-methylpyridin-3-yl) ethyl methanesulfonate To a stirred solution of <strong>[100189-17-1]2-(6-methylpyridin-3-yl)ethan-1-ol</strong> (0.5 g, 3.6 mmol) in dry DCM (10 mL) at 0 C was added triethyl amine (1.5 mL, 10.8 mmol, Spectrochem) followed by addition of methane sulfonyl chloride (0.4 mL, 5.4 mmol, Spectrochem). Reaction mass was brought to RT and stirred for 1 h. Reaction completion was monitored by TLC. Reaction mass was diluted with DCM, washed with water, dried over Na2SO4 and evaporated. The crude was isolated as pale brown liquid and was taken for next step without any further purification (0.36 g, 46%). 1H NMR (400 MHz, DMSO-d6): delta 8.63 (s, 1 H), 8.00 (dd, J = 8.0, 1.8 Hz, 1 H), 7.62-7.58 (m, 1 H), 4.45 (t, J = 6.4 Hz, 2H), 3.14 (s, 3H), 3.07 (d, J = 6.4 Hz, 2H), 2.59 (s, 3H). LCMS: (Method A) 216.0 (M+H)+, Rt. 3.3 min, 50.2% (Max). |
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