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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Structure of 1822-51-1
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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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CAS No. : | 1822-51-1 |
Formula : | C6H7Cl2N |
M.W : | 164.03 |
SMILES Code : | ClCC1=CC=NC=C1.[H]Cl |
MDL No. : | MFCD00012826 |
InChI Key : | ZDHKVKPZQKYREU-UHFFFAOYSA-N |
Pubchem ID : | 74570 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H301-H314-H315-H317-H335 |
Precautionary Statements: | P261-P280-P301+P310-P305+P351+P338-P310 |
Class: | 8(6.1) |
UN#: | 2923 |
Packing Group: | Ⅲ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.96 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.48 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.37 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.69 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.63 |
Solubility | 0.382 mg/ml ; 0.00233 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.04 |
Solubility | 1.49 mg/ml ; 0.00907 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.0 |
Solubility | 0.162 mg/ml ; 0.000989 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 |
-5.78 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 |
2.0 |
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 |
1.0 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) |
1.18 |
* 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 |
---|---|---|
62% | With potassium acetate; In propan-1-ol; at 70℃; for 8h; | Example 119: 4-(4-Chlorophenylsulfonylmethyl)pyridine Under heating, a 1-propanol (50 ml) solution of 4-chloromethylpyridine hydrochloride (1.26 g, 7.65 mmol), <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (1.52 g, 7.65 mmol) and potassium acetate (1.50 g, 15.3 mmol) was stirred at 70C for 8 hours.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue was filtered through a short column (silica gel, ethyl acetate) and the elude was concentrated under reduced pressure.. The residue was subjected to chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate (=2:3) elude was concentrated under reduced pressure, whereby the title compound (1.26 g, 62%) was obtained as a white solid.1H-NMR (400MHz, CDCl3) δ: 4.29(2H,s), 7.06(2H,d,J=6.1Hz), 7.47(2H,d,J=8.8Hz), 7.59(2H,d,J=8.5Hz), 8.57(2H,d,J=6.1Hz). MS (m/z): 268 (M++H). |
62% | With potassium acetate; In propan-1-ol; at 70℃; for 8h; | A 1-propanol (50 ml) solution of 4-chloromethylpyridine hydrochloride (1.26 g, 7.65 mmol), <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (1.52 g, 7.65 mmol) and potassium acetate (1.50 g, 15.3 mmol) was stirred under heating at 70C for 8 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue thus obtained was caused to pass through a short column (silica gel, ethyl acetate) and the eluate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, and the fraction obtained from the hexane:ethyl acetate (=2:3) eluate was concentrated under reduced pressure to give the title compound (1.26 g, 62%) as a white solid. 1H-NMR(400MHz, CDCl3) δ: 4.29(2H,s), 7.06(2H,d,J=6.1Hz), 7.47(2H,d,J=8.8Hz), 7.59(2H,d,J=8.5Hz), 8.57(2H,d,J=6.1Hz). MS (m/z) : 268 (M++H). |
With potassium acetate; In butan-1-ol; at 70℃; for 5h; | Example 74: 4-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]pyridine <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (207 mg, 1.04 mmol), 3-chloromethylpyridine hydrochloride (171 mg, 1.04 mmol) and potassium acetate (204 mg, 2.08 mmol) were added to n-butanol (5 ml).. The resulting mixture was stirred at 70C for 5 hours.. After cooling to room temperature, the solvent was concentrated under reduced pressure.. To the residue was added ethyl acetate and from the resulting mixture, the insoluble matter was filtered off.. The filtrate was concentrated under reduced pressure.. The residue was subjected to chromatography on a silica gel column and the from the fraction eluted with hexane:ethyl acetate (=2:3), a white solid (117 mg) was obtained. Then, a toluene (10 ml) solution of the resulting solid (52 mg), the 4-(methylsulfonyl)-1-butanol (90 mg, 0.592 mmol) obtained in Referential Example 3 and cyanomethylenetri-n-butylphosphorane (140 mg, 0.582 mmol) was heated under reflux for 2 days under an argon atmosphere.. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In water; | PREPARATION 18 A mixture of <strong>[58909-39-0]2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine</strong> (15.91 g), 4-chloromethylpyridine hydrochloride (19.68 g) and sodium bicarbonate (33.6 g) in water (500 ml) was stirred for 2 hours at 45 C. The mixture was cooled to 10 C. and adjusted to pH 6.2 with 6N hydrochloric acid. The resulting precipitates were collected by filtration, washed with water and acetone, and dried to give 2-methyl-3-(4-pyridylmethylthio)-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (17.2 g), mp. 219 to 222 C. (dec.). IR (nujol): 3480, 3400, 1700, 1630, 1605, 1500 cm-1. NMR (DMSO-d6 +D2 O, delta): 3.63 (3H, s), 4.43 (2H, s), 7.3-7.6 (2H, m), 8.4-8.6 (2H, m). |
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