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Type | HazMat fee for 500 gram (Estimated) |
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Structure of 3747-74-8
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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.
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CAS No. : | 3747-74-8 |
Formula : | C10H9Cl2N |
M.W : | 214.09 |
SMILES Code : | ClCC1=NC2=CC=CC=C2C=C1.[H]Cl |
MDL No. : | MFCD00012734 |
InChI Key : | WDETYCRYUBGKCE-UHFFFAOYSA-N |
Pubchem ID : | 3083823 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302+H312-H314 |
Precautionary Statements: | P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.1 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 58.47 |
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 |
3.42 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.62 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.72 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.43 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.64 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.83 |
Solubility | 0.032 mg/ml ; 0.00015 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.37 |
Solubility | 0.0912 mg/ml ; 0.000426 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.72 |
Solubility | 0.00409 mg/ml ; 0.0000191 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.18 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 |
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) |
1.53 |
* 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 |
---|---|---|
EXAMPLE 2 (Compound 2)Quinoline-2-(methyleneaminophenoxyisobutyric) Acid; A mixture of 1.95 g (0.01 mole) of 4-aminoiphenoxyisobutyric acid, 2.28 g (0.01 mole) of 2-chloromethylquinoline hydrochloride; 3 g of potassium carbonate,40 ml of water and 29 ml of isopropanol is refluxed and stirred for 24 hours and a dark brown solution with about 1 g of product is obtained. The product is worked up by adding sodium carbonate. Dithionite is added and the mixture is acidified with acetic acid and a brown powder is obtained. The structure is set forth as structure 2..C20H20N2O3; mw 336 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 60℃; for 1.5h; | To a mixture of <strong>[5470-65-5]3-bromo-4-nitrophenol</strong> (26, 4.91 g, 22.5 mmol), 2-(chloromethyl)quinoline hydrochloride (5.79 g, 27.0 mmol) and potassium iodide (374 mg, 2.25 mmol) in DMF (50 mL) was added K2CO3 (7.47 g, 54.1 mmol), and the mixture was stirred at 60 °C for 90 min. After cooling at room temperature, the mixture was diluted with EtOAc, and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was washed with EtOAc?hexane to give 27 (6.89 g, 85percent) as a pale yellow solid. 1H NMR (CDCl3) delta 5.44 (s, 2H), 7.03?7.07 (m, 1H), 7.42 (d, 1H, J = 2.4 Hz), 7.55?7.62 (m, 2H), 7.74?7.80 (m,1H), 7.85 (d, 1H, J = 8.3 Hz), 7.96 (d, 1H, J = 9.3 Hz), 8.09 (d, 1H, J = 8.8 Hz), 8.23 (d, 1H, J = 8.3 Hz); MS (ESI) m/z 359, 361 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-Butylimidazole (0.927 g, 7.46 mmol) dissolvedin acetonitrile (15 mL) was combined with potassium hydroxide (0.439 g, 9.23mmol) and stirred at 80C for 30 minutes. 2-(Chloromethyl)quinolinehydrochloride (1.27 g, 5.93 mmol), and potassium hydroxide (0.335 g, 5.97 mmol)were added to the reaction mixture which was heated at 80C overnight. The mixture was filtered toremove a white solid (presumed to be potassium chloride) and the volatiles wereremoved from the filtrate to yield a yellow oil. The oil was diluted withdichloromethane (30 mL) and washed with a basic aqueous solution (2 x 25 mL)and water (25 mL). The organic layer was dried with magnesium sulfate and thevolatiles were removed. The resulting yellow oil was resuspended inacetonitrile and 2-(chloromethyl)quinoline (1.14 g, 6.42 mmol) was added. Thereaction mixture was heated overnight at 80C. 11 precipitated from hot acetonitrile and was washed with coldacetonitrile (0.238 g, 9% yield).Mp: 196-198C. Found C, 69.5; H, 6.3; N, 12.1%.Calculated for C27H27N4Cl1: C,73.2; H, 6.1; N, 12.7%. Calculated for C26H25N4Cl1?H2O: C, 70.4; H, 6.3; N, 12.2%. HRMS (ESI+) calcd for C27H27N4+[M-Cl] of m/z = 407.2230, found m/z = 407.2199.1H NMR (500 MHz, DMSO- d6)delta = 8.51 (2H, d, Ar, J = 8.6 Hz), 8.04 (2H, d, Ar, J = 8.1 Hz), 7.97 (2H, s,Ar), 7.83 (2H, d, Ar, J = 8.3 Hz), 7.77 (2H, m, Ar), 7.64 (4H, m, Ar) 5.93 (4H, s, CH2), 3.12 (2H, q, CH2,J = 7.9 Hz), 1.24 (2H, m, CH2), 1.14 (2H, m, CH2), 0.51 (3H, t, CH3, J = 7.2 Hz). 13CNMR (125 MHz, DMSO- d6) delta= 154.4 (Ar), 148.7 (Ar), 146.8 (Ar), 137.5 (Ar), 130.1 (Ar), 128.4 (Ar), 128.0 (Ar), 127.2 (Ar), 127.0 (Ar), 122.9 (Ar),119.8 (Ar), 52.5 (CH2), 28.4 (CH2), 22.8 (CH2),21.5 (CH2), 13.1 (CH3). MS: m/z = 406.9 (theorfor M+ C27H27N4+ =407.2).Crystal data for 11-PF6?1.5(H2O):C54H60F12N8O3P2,M = 1159.04, Monoclinic, a = 15.1142(7) A, b = 48.741(2) A, c =7.3043(3) A, V = 5345.1412) A3, T = 100(2) K, space group P21/c,Z = 4, 53996 reflections measured,10736 [R(int) = 0.0592]. The final R1values were 0.0600 (I > 2sigma(I)).The final wR(F2) values were 0.1274 (I > 2sigma(I)). The final R1 values were 0.0913 (all data). The final wR(F2)values were 0.1433 (all data). |
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