Structure of 83802-71-5
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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. : | 83802-71-5 |
Formula : | C10H9FO2 |
M.W : | 180.18 |
SMILES Code : | O=C1CCC2=C1C=C(OC)C(F)=C2 |
MDL No. : | MFCD09261202 |
InChI Key : | FFZRFPIFJVKURP-UHFFFAOYSA-N |
Pubchem ID : | 13059023 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.94 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.03 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.74 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.38 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.76 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.14 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.21 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.33 |
Solubility | 0.845 mg/ml ; 0.00469 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.91 |
Solubility | 2.22 mg/ml ; 0.0123 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.52 |
Solubility | 0.0542 mg/ml ; 0.000301 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 |
-6.16 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) |
1.86 |
* 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 |
---|---|---|
91% | Reference Example 9 5-Fluoro-6-methoxy-1-indanone In the same manner as in Reference Example 6, the target compound was obtained from 3-(3-fluoro-4-methoxyphenyl)propionic acid. The yield was 91percent. m.p.: 152-153° C. (recrystallized from methanol/ethyl acetate); NMR (CDCl3) delta: 2.71 (2H, t, J=5.7 Hz), 3.08 (2H, t, J=5.7 Hz), 3.92 (3H, s), 7.17 (1H, d, J=10.3 Hz), 7.29 (d, J=8.1 Hz); Elemental Analysis for C10 H9 FO2: Calcd.: C 66.66; H 5.03; Found: C 66.82; H 5.06 | |
A mixture of Compound II (900 mg), toluene (9 mL) and thionyl chloride (393 muL) was stirred at 90° C. for one hour, and concentrated under reduced pressure. The obtained residue was added to an ice-cold solution of aluminium chloride (605 mg) in methylene chloride (45 mL), and the mixture was stirred for one hour. The reaction solution was added dropwise into ice-cold water, and the mixture was stirred for one hour, ane extracted with ether. The organic layer was washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give Compound III (666 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Reference Example 10 (E)-(5-fluoro-6-methoxyindan-1-ylidene) acetonitrile In the same manner as in Reference Example 7, the target compound was obtained from <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> and diethyl cyanomethylphosphonate. The yield was 75percent. m.p.: 197-199° C. (recrystallized from hexane/ethyl acetate); NMR (CDCl3) delta: 3.00-3.19 (4H, m), 3.92 (3H, s), 5.53 (1H, t, J=2.2 Hz), 7.02 (1H, d, J=7.6 Hz), 7.07 (1H, d, J=10.3 Hz); Elemental Analysis for C12 H10 FNO: Calcd.: C 70.93; H 4.96; N 6.89; Found: C 70.65; H 5.13; N 6.99 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 4 4-(6-fluoro-indan-1-yl)piperidine This compound was prepared in two steps from 4-bromopyridine and <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> as described in method 2 above to give the product as the HCl salt (66percent, mp: 178°-179° C.). Anal. Calc'd for C15 H2 FNOodsold;HCl: C, 63.04percent; H, 7.41percent; N, 4.90percent. Found: C, 62.80percent; H, 7.30percent; N, 4.70percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 7 1-(5-fluoro-6-methoxy-indan-1-yl)piperazine 3-Fluoro-4-methoxybenzaldehyde was converted to 5-fluoro-6-methoxy-1-indanone by method 2, steps 1-4 above, (92percent, mp 149°-151° C.). Anal. Calc'd for C10 H9 FO2: C, 66.66percent; H, 5.03percent. Found: C, 66.65percent; H, 4.96percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium borohydrid;titanium(IV) isopropylate; | 1-Formyl-piperazine (2.1 g, 20 mmol), 5-fluoro-6-methoxy-indan-1-one (1.8 g, 10 mmol), titanium(IV) isopropoxide (5 ml, 15 mmol), and sodium borohydride (1.2 g, 30 mmol) were reacted by Method B to give the product (2.2 g, 88percent, mp 163°-166° C.). Calcd for C14 H19 FN2 O.C4 H4 O4.0.1H2 O: C, 56.23percent; H, 6.56percent; N, 7.28percent. Found: C, 56.65percent; H, 6.41percent; N, 6.98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Reference Example 23 5-Fluoro-6-methoxy-1-indanone Starting with 3-(3-fluoro-4-methoxyphenyl)propionic acid, the title compound was synthesised in otherwise the same manner as Reference Example 11 (yield 94percent). m.p. 152-154° C. NMR(CDCl3) delta: 2.70(2H,t,J=5.5 Hz), 3.07(2H,t,J=5.5 Hz), 3.91(3H,s), 7.17(1H,d,J=10.3 Hz), 7.29(1H,d,J=10.3 Hz). Elemental analysis for C10 H9 FO2: Calcd.: C, 66.66; H, 5.03. Found: C, 66.85; H, 4.97. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Reference Example 24 (E)-(5-Fluoro-6-methoxyindan-1-ylidene)acetonitrile Starting with <strong>[83802-71-5]5-fluoro-6-methoxy-1-indanone</strong> and diethyl cyanomethylphosphate, the title compound was synthesised in otherwise the same manner as Reference Example 8 (yield 73percent). m.p. 197-199° C. NMR(CDCl3) delta: 3.00-3.19(4H,m), 3.91(3H,s), 5.52(1H,br s), 6.99-7.10(2H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron tribromide; In dichloromethane; at 20℃; for 7h;Cooling with ice; | To an ice-cold solution of Compound III (666 mg) in methylene chloride (15 mL) was added dropwise boron tribromide (4.44 mL), and the mixture was stirred at room temperature for 7 hours. The reaction solution was cooled with ice, and thereto was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to give Compound III (52 mg). |
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