Structure of 889865-34-3
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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. : | 889865-34-3 |
Formula : | C22H34BNO5 |
M.W : | 403.32 |
SMILES Code : | CC1(C)C(C)(C)OB(C2=CC=C(OC3CCN(C(OC(C)(C)C)=O)CC3)C=C2)O1 |
MDL No. : | MFCD22418284 |
InChI Key : | XPNSYBYHVPMAET-UHFFFAOYSA-N |
Pubchem ID : | 59320843 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 29 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.68 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 119.08 |
TPSA ? Topological Polar Surface Area: Calculated from |
57.23 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 |
4.32 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.38 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.19 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.39 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.46 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.82 |
Solubility | 0.00611 mg/ml ; 0.0000152 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.24 |
Solubility | 0.00234 mg/ml ; 0.00000581 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.05 |
Solubility | 0.0036 mg/ml ; 0.00000893 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) |
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) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.69 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 |
0.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.74 |
* 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% | Palladium acetate (0.021 g, 0.094 mmol) and triphenylphosphine (0.10 g, 0.38 mmol) were combined in a flask in 1,4-dioxane (6.0 mL). After stirring for 30 mi DMF (5.7 g, 6.0 mL, 78 mmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxyj piperidine- 1- carboxylate (0.75 g, 1.9 mmol), 7-bromoimidazo[1,2-ajpyridine (0.44 g, 2.2 mmol) and aq. Na2CO3 (0.5 M) (12.0 mL, 6.0 mmol) were added and the flask was heated under nitrogen at 90C overnight. The mixture was diluted with water (60 mL) then extracted with EtOAc (3x50 mL). The organic extracts were combined, washed with brine (50 mL), dried over sodium sulfate filtered and concentrated in vacuo. The residue was dissolved in EtOAc (40 mL) then treated with 2M HC1 in ether (1.5 mL) with stirring. The resultant solids were collected by filtration, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.039 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere; | A mixture of <strong>[876343-10-1]4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine</strong> (Synnovator, Inc., CAS[ 876343-10-1]) (855 mg, 3.06 mmol), Cs2C03 (2492 mg, 7.65 mmol) and tert-butyl 4-(4-(4,4,5,5-tetramethyl- 1 ,3, 2-dioxaborolan-2-yl)phenoxy)piperidine-1 -carboxylate (step 1) (1234 mg, 3.06 mmol) in dioxane/water 1 :1 (30 ml) was degassed with argon. PdCl2(dppf)-CH2Cl2 adduct (250 mg, 0.306 mmol) was added and the RM was stirred at 100C for 3 h. The RM was cooled to RT and then partitioned between EtOAc and sat. aq. NaHC03. Layers were separated, then the organic layer was washed with brine, dried over MgS04 and concentrated under reduced pressure. Purification of the crude product by flash chromatography on silica gel eluting with 0 - 100% EtOAc in CHX afforded a brown residue. The residue was then triturated with MeOH, the resulting suspension was filtered, washed with Et20 and dried under reduced pressure to afford 1.039 g of the title compound as a beige powder. LC-MS (Method A): Rt = 1.24 min, [M+H]+ = 429.3/431.2. |
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