Structure of 876-32-4
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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. : | 876-32-4 |
Formula : | C9H14ClNO |
M.W : | 187.67 |
SMILES Code : | Cl.COC1=CC=C(CNC)C=C1 |
MDL No. : | MFCD04117881 |
Boiling Point : | No data available |
InChI Key : | NNANAKYVZOHKHW-UHFFFAOYSA-N |
Pubchem ID : | 17292353 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 52.47 |
TPSA ? Topological Polar Surface Area: Calculated from |
21.26 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 |
2.16 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.83 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.83 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.58 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.54 |
Solubility | 0.546 mg/ml ; 0.00291 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.24 |
Solubility | 1.08 mg/ml ; 0.00577 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.35 |
Solubility | 0.0838 mg/ml ; 0.000447 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 |
-5.91 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 |
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) |
1.0 |
* 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 |
---|---|---|
51% | With sodium hydroxide; In tetrahydrofuran; water; at 65℃; for 2h;Sealed tube; | In a sealed tube, mixture of benzamide 3a (38 mg, 0.11 mmol), formaldehyde (37% in water, 0.043 mL, 0.55 mmol), l-(4-methoxyphenyl)-N-methylmethanamine hydrochloride (102 mg, 0.55 mmol), and 1 N NaOH (0.5 mL) in H2O:THF (1 mL: 0.5 mL) was heated at 65 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over Na2S04, and concentrated, then purified by column chromatography to afford the pure product (28 mg, 51% yield) as off white solid. 1H NMR (CDCI3, 300 MHz) 6: 8.00 (d, J= 1.8 Hz, 1H), 7.82 (d, J= 8.7 Hz, 1H), 7.40 (dd, J= 2.1, 8.7 Hz, 1H), 7.23 (d, J= 8.7 Hz, 2H), 7.14- 7.07 (m, 1H), 6.90-6.83 (m, 1H), 6.85 (d, J= 7.8 Hz, 2H), 6.20 (bs, 1H), 5.50 (s, 2H), 4.39 (d, J= 6.3 Hz, 2H), 3.79 (s, 3H), 3.60 (s, 2H), 2.33 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide; In tetrahydrofuran; water; at 65℃; for 2h;Sealed tube; | In a sealed tube, mixture of benzamide 5a (38 mg, 0.11 mmol), formaldehyde (37% in water, 0.043mL, 0.55 mmol), <strong>[876-32-4]1-(4-methoxyphenyl)-N-methylmethanamine hydrochloride</strong> (102 mg, 0.55 mmol), and 1N NaOH (0.5 mL) in H2O:THF (1mL:0.5 mL) was heated at 65 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over Na2SO4, and concentrated, then purified by column chromatography to afford the pure product (28 mg, 42% yield) as off white solid. 1H NMR (CDCl3, 300 MHz) delta: 8.57 (d, J= 2.1 Hz, 1H), 8.24 (d, J= 3.0 Hz, 1H), 7.23 (d, J= 8.7 Hz, 2H), 7.15- 7.08 (m, 1H), 6.91-6.83 (m, 1H), 6.85 (d, J= 7.8 Hz, 2H), 6.25 (bs, 1H), 5.48 (s, 2H), 4.39 (d, J= 6.0 Hz, 2H), 3.79 (s, 3H), 3.60 (s, 2H), 2.33 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With sodium hydroxide; In tetrahydrofuran; water; at 65℃; for 2h;Sealed tube; | In a sealed tube, mixture of benzamide 24b (38 mg, 0.11 mmol), formaldehyde (37% in water, 0.043 mL, 0.55 mmol), <strong>[876-32-4]1-(4-methoxyphenyl)-N-methylmethanamine hydrochloride</strong> (102 mg, 0.55 mmol), and 1N NaOH (0.5 mL) in H2O:THF (1 mL:0.5 mL) was heated at 65 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over Na2SO4, and concentrated, then purified by column chromatography to afford the pure product (28 mg, 57% yield) as off white solid. 1H NMR (CDCl3, 300 MHz) delta: 7.73 (d, J= 1.8 Hz, 1H), 7.49 (d, J= 8.7 Hz, 1H), 7.36 (dd, J= 1.8, 8.7 Hz, 1H), 7.23 (d, J= 8.7 Hz, 2H), 7.20- 7.13 (m, 1H), 6.91-6.84 (m, 1H), 6.85 (d, J= 8.7 Hz, 2H), 6.17 (bs, 1H), 5.35 (s, 2H), 4.38 (d, J= 6.3 Hz, 2H), 3.79 (s, 3H), 3.59 (s, 2H), 2.32 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(2-methoxyethylamino)-1,6-naphthyridin-2(1H)-one; In 1,4-dioxane; at 180℃; for 4h;Inert atmosphere; | A mixture of 3-(3-amino-4-fluorophenyl)-7-chloro-1-isopropyl-1,6-naphthyridin-2(1H)-one (4 g, 12.1 mmol) and (4-methoxybenzyl)methylamine (15 mL) was degassedunder reduced pressure, then heated to 180C under N2 for 4 h. After cooling, the reactionmixture was diluted with Et20. The precipitate was filtered, washed with Et20 and dried invacuo to giVe 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-[( 4-methoxybenzyl)-methylamino]-1H-[1,6]naphthyridin-2-one (5.3 g) as a solid contaminated with (4-methoxybenzyl)methylamine HCl salt. |