Structure of 51207-86-4
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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.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 51207-86-4 |
| Formula : | C11H14N2O2 |
| M.W : | 206.24 |
| SMILES Code : | NC1=CC=C(C=C1)C(=O)N1CCOCC1 |
| English Name : | (4-Aminophenyl)(morpholino)methanone |
| MDL No. : | MFCD00158788 |
| InChI Key : | WEHVQIQNGXWTME-UHFFFAOYSA-N |
| Pubchem ID : | 577815 |
| Num. heavy atoms | 15 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.36 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 61.24 |
| TPSA ? Topological Polar Surface Area: Calculated from |
55.56 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.74 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.33 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.37 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.58 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.07 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.82 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-1.49 |
| Solubility | 6.66 mg/ml ; 0.0323 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.06 |
| Solubility | 17.9 mg/ml ; 0.087 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.18 |
| Solubility | 1.37 mg/ml ; 0.00662 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 |
No |
| 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 |
-7.32 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<1.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.32 |
* 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 |
|---|---|---|
| 44% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane Reflux; | 2 Step 2. Preparation of [4-(6-Bromo-imidazo[1,2-a]pyridin-8-ylamino)-phenyl]-morpholin-4-yl-methanone Step 2. Preparation of [4-(6-Bromo-imidazo[1,2-a]pyridin-8-ylamino)-phenyl]-morpholin-4-yl-methanone 6-Bromo-8-iodo-imidazo[1,2-a]pyridine (500 mg, 1.53 mmol), (4-aminophenyl)(morpholino)-methanone (348 mg, 1.69 mmol) and CsCO3 (998 mg, 3.06 mmol) were dissolved in dioxane (10 ml). Under N2 atmosphere, Pd2(dba)3 (70 mg, 0.077 mmol) and Xantphos (89 mg, 0.153 mmol) were added and the mixture was stirred at reflux temperature overnight. After the completion of the reaction, the mixture was cooled to room temperature, poured into water (100 mL) and extracted with DCM (100 ml). The organic extracts were washed with saturated aqueous solution of sodium chloride (100 ml), dried over sodium sulfate and concentrated. The residue was purified by silica gel column (petroleum ether: ethyl acetate 1:2) to afford the desired product as a yellow solid (270 mg, yield 44%). LC-MS: 401[M+1]+, tR=1.257 min. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 20℃; for 1h; | [00422] In a microwave vial containing <strong>[3177-24-0]2,4-dichloro-pyrimidine-5-carbonitrile</strong> (250.00 mg;1.44 mmol; 1.00 eq.) in butan-1-ol (10.00 ml; 110.09 mmol; 76.62 eq.) at 0C was added DIPEA(0.71 ml; 4.31 mmol; 3.00 eq.) and (4-Amino-phenyl)-morpholin-4-yl-methanone (296.35 mg;1.44 mmol; 1.00 eq.). The mixture was stuffed at rt for lh before it was concentrated and carriedto the next step. MS: mlz = 344 [M+H]+. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 45% | With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 16h; | 4.3.1 Procedure for substitution with (4-aminophenyl) (morpholino)methanone To a stirred solution of commercially available 2,6-dichloro-3-nitropyridin-4-amine 1 or 4,6-dichloro-3-nitropyridin-2-amine 50 (both 500mg, 2.4mmol, 1 eq) in anhydrous DMF (7mL), (4-aminophenyl) (morpholino)methanone (544mg, 2.64mmol, 1.1 eq) and DIPEA (435μL, 2.64mmol, 1.1 eq) were added. The resulting mixture was stirred at 100°C for 16h followed by LC/MS analysis that was used to confirm the full conversion to the corresponding products 2 or 51. The resulting mixture was cooled to ambient temperature and then diluted with brine (150mL) and extracted with EtOAc (5×150mL). Organic extracts were combined, dried over MgSO4, filtered and evaporated under reduced pressure. The crude products were purified by FCC (gradient elution with CH2Cl2/EtOAc (1:1, v/v) to CH2Cl2/EtOAc/methanol (1:1:0.1, v/v)) to afford products that were yellow solids (2: 430mg, 47% yield; 51: 410mg, 45% yield). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92 % | With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); Xantphos In 1,4-dioxane at 110℃; Schlenk technique; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); Xantphos; potassium phosphate / 1,4-dioxane / 110 °C / Schlenk technique; Inert atmosphere 2: [Ru(p-cymene)Cl2]2; manganese (II) acetate tetrahydrate / 2,2,2-trifluoroethanol / 16 h / 110 °C / Schlenk technique; Inert atmosphere |

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