Structure of 35490-90-5
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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. : | 35490-90-5 |
Formula : | C7H6ClNO |
M.W : | 155.58 |
SMILES Code : | O=CC1=C(Cl)C=CC=C1N |
MDL No. : | MFCD10696880 |
InChI Key : | RNEANOJBDLVBRF-UHFFFAOYSA-N |
Pubchem ID : | 22399512 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.24 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.44 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.9 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.67 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.37 |
Solubility | 0.668 mg/ml ; 0.0043 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.41 |
Solubility | 0.61 mg/ml ; 0.00392 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.59 |
Solubility | 0.402 mg/ml ; 0.00258 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 |
-5.91 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 |
2.0 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) |
1.02 |
* 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 |
---|---|---|
96% | With manganese(IV) oxide In diethyl ether for 0.5 h; | To prepare this compound, manganese dioxide (13.6 g, 157 mmol) was added to a solution of 2-(amino-6-chlorophenyl)methanol (2.75 g, 17.5 mmol) in 150 mL diethyl ether. The mixture was stirred for 0.5 hours then filtered through celite and rinsed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford 2.62 g(96percent) of 2-amino-6-chlorobenzaldehyde. |
85% | With manganese(IV) oxide In dichloromethane at 20℃; for 23 h; Inert atmosphere | General procedure: To a solution of 1a (1.2 g, 7.61 mmol) in CH2Cl2 (20 mL) was added MnO2 (2.6 g, 30.1 mmol) and stirred at rt under an Ar atmosphere. After 23 h with stirring, the reaction mixture was filtrated and evaporated. The residue was crystallized from AcOEt to give 7a (1.0 g, 85percent) as a yellow needle crystal. Mp 96–97 °C. IR (KBr): 3422, 3315, 1650, 1624, 1542, 1398, 1234, 919, 772 cm−1. 1H NMR (400 MHz, CD3OD) δ: 6.60 (1H, dd, J = 0.8, 7.6 Hz), 6.68 (1H, td, J = 0.8, 8.4 Hz), 7.18 (1H, dd, J = 7.6, 8.4 Hz), 10.41 (1H, d, J = 0.8 Hz). 13C NMR (100 MHz, CD3OD) δ: 114.6, 117.0, 117.5, 136.7, 140.2, 154.6, 193.3. HRMS (EI) Calcd for C7H6ClNO [M]+: 155.0138. Found: 155.0141. |
10% | With manganese(IV) oxide In diethyl ether at 20℃; for 6 h; | 2.30 g (14.6 mmol) of (2-amino-6-chlorophenyl)methanol prepared in step 1, MnO2 (10 equivalent), and diethylether (50 mL) were mixed together, which was stirred at room temperature for 6 hours. The reaction mixture was filtered with celite pad, and concentrated under reduced pressure. The residue was separated by column chromatography (SiO2, eluent: hexane/CH2Cl2, 5/1->CH2Cl2) to give 2.27 g of the target compound 2-amino-6-chlorobenzaldehyde as a yellow solid (14.6 mmol, yield: 10percent). 1H NMR(300 MHz, CDCl3) δ 10.48 (s, 1H) , 7.17 (t, J=8.2 Hz, 1H), 6.67 (d, J=7.7 Hz, 1H), 6.54 (d, J=8.4 Hz, 1H) , 6.48 (br s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45 %Spectr. | With vasicine In ethylene glycol at 80℃; for 48 h; | General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product. |
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