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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 74879-18-8
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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.
4.5
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 74879-18-8 |
Formula : | C5H12N2 |
M.W : | 100.16 |
SMILES Code : | N1[C@H](CNCC1)C |
MDL No. : | MFCD00171452 |
InChI Key : | JOMNTHCQHJPVAZ-YFKPBYRVSA-N |
Pubchem ID : | 2734219 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H228-H315-H319-H335 |
Precautionary Statements: | P210-P240-P241-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P405-P501 |
Class: | 4.1 |
UN#: | 1325 |
Packing Group: | Ⅱ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 37.47 |
TPSA ? Topological Polar Surface Area: Calculated from |
24.06 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.49 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.78 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.19 |
Solubility | 64.7 mg/ml ; 0.645 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.39 |
Solubility | 246.0 mg/ml ; 2.45 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.17 |
Solubility | 6.77 mg/ml ; 0.0676 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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 |
-7.22 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) |
1.44 |
* 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 |
---|---|---|
69% | With triethylamine; In N,N-dimethyl-formamide; at 20.0℃; for 14.0h; | Triethylamine (4.13 g, 3 niL, 40.8 mmol, 4 eq) is added to a solution of 6-chloro- nicotinonitrile (1.38 g, 10 mmol, leq), (S)-2-methyl- piperazine (1.0Og, 10 mmol, leq) in DMF (15 niL), and the resulting solution is stirred at rt for 14 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (1.4 g, 69%). 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 8.38 (s, 1 H), 7.58 (d, J=9.60 Hz, 1 H), 6.59 (d, J=9.09 Hz, 1 H), 4.19 - 4.31 (m, 2 H), 3.08 - 3.15 (m, 1 H), 2.92 - 3.04 (m, 1 H), 2.81 - 2.91 (m, 2 H), 2.57 - 2.65 (m, 1 H), 1.15 (d. J=6.32 Hz, 3 H). |
67% | With potassium carbonate; In N,N-dimethyl acetamide; at 60.0℃; for 2.0h; | To a stirred solution of (2S)-2-methylpiperazine (0.30 g, 2.1 mmol) in DMA (6 mL), 6-chloropyridine-3-carbonitrile (0.29 g, 2.3 mmol) and K2C03 were added. The resultantreaction mixture was heated to 60 C for 2 h (TLC indicated complete consumption ofstarting material). The reaction mixture was diluted with cold water (20 mL) and extractedwith EtOAc (3 x 25 mL). The combined organic extracts were washed with cold water (20mL) and brine (2 x 20 mL). The organic layer was separated, dried over Na2S04 andconcentrated under reduced pressure to give the crude residue which was purified by columnchromatography (100-200 silica gel, 10 g, 10% MeOH-DCM) to furnish 6-[(3S)-3-methylpiperazin-1-yl]pyridine-3-carbonitrile (0.29 g, 67%) as an off-white solid.LCMS: m/z: 203.4 [M+Ht. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[19064-24-5]2,6-difluoronitrobenzene</strong> (1.0 g, 6.3 mMol) in dimethylsulfoxide (7 mL) was added sodium azide (0.45 g, 6.9 mMol). After stirring for 2 h at 20 C. diisopropylethylamine (0.81 g, 6.3 mMol, 1.1 mL) was added to the reaction mixture followed by S-2-methylpiperazine (0.95 g, 9.5 mMol). The reaction mixture stirred at 60 C. for 10 h then 20 C. for an additional 12 h at which point it was diluted with ethyl acetate (50 mL), washed with 1N sodium hydroxide solution (20 mL) and water (2×20 mL). The organic layer was dried (MgSO4), evaporated and the residue dissolved in dichloromethane (25 mL) and treated with di-t-butyldicarbonate (1.5 g, 7.1 mMol). After stirring for 16 h at 20 C. the solvent was evaporated and the residue was chromatographed on silica gel eluted with 75% hexanes in ethyl acetate to provide the product as a yellow gum (2.2 g, 96%). 1H-NMR (CDCl3), δ=7.42 (dd, 1H, J=8.2 Hz, J=8.2 Hz), 7.0 (d, 1H, J=8.2 Hz), 6.95 (d, 1H, J=8.2 Hz), 4.28 (bm, 1H), 3.88 (bd, 1H, J=13.3 Hz), 3.00 (m, 5H), 1.48 (s, 9H), 1.22 (d, 3H, J=6.8 Hz). LC/MS (Method A), rt=2.05 mins., purity=89.8%, calculated mass=362, [M+H-C5H9O2]+=263. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80 mg | In ethanol; at 80℃; for 8.0h;Microwave irradiation; | A mixture of <strong>[76006-11-6]7-chloro-1H-pyrazolo[3,4-c]pyridine</strong> (200 mg, 1.30 mmol) and (S?)-2- methylpiperazine (1.30g, 13.02 mmol) was dissolved in CH3CH2OH (20 mL). The mixture was stirred at 80 C for 8 h in microwave radiation. The solution was purified by prep-HPLC (Boston C18 21*250mm 1O.im, Mobile phase: A: 0.1 % trifluoroacetic acid; B: acetonitrile) to afford (S)7-(3-methylpiperazin-1-yl)-1H-pyrazolo[3,4-c]pyridine (80 mg, 0.37 mmol) as a white solid. MS (EI+, m/z): 218.2 [M+H]t ?H NIVIR (400 IVIFIz, DMSO-d6) 8.15 (s, 1H), 7.63 (d, J 5.7 Hz, 1H), 7.02 (d, J= 5.7 Hz, 1H), 4.39 (s, 2H), 3.04-2.68 (m, 4H), 2.46 (s, 2H), 1.03 (d, J = 6.3 Hz, 3H). |