Structure of 4-Morpholinoaniline
CAS No.: 2524-67-6
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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. : | 2524-67-6 |
| Formula : | C10H14N2O |
| M.W : | 178.23 |
| SMILES Code : | NC1=CC=C(N2CCOCC2)C=C1 |
| MDL No. : | MFCD00006169 |
| InChI Key : | PHNDZBFLOPIMSM-UHFFFAOYSA-N |
| Pubchem ID : | 75655 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 13 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.4 |
| Num. rotatable bonds | 1 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 56.57 |
| TPSA ? Topological Polar Surface Area: Calculated from |
38.49 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.71 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.68 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.73 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.83 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.25 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.04 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-1.65 |
| Solubility | 4.0 mg/ml ; 0.0224 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.07 |
| Solubility | 15.3 mg/ml ; 0.0861 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.22 |
| Solubility | 1.07 mg/ml ; 0.006 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) |
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) |
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 |
-6.9 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 |
2.0 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) |
1.43 |
* 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.

[ 2524-67-6 ]
[ 483324-01-2 ]
[ 464213-93-2 ]
[ 2524-67-6 ]
[ 37091-73-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine; In dichloromethane; | Example 110 N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-morpholinoaniline 4-Morpholinoaniline (0.286 g, 1.60 mmol), triethylamine (0.162 g, 1.60 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.271 g, 1.60 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexane: ethyl acetate = 1:2) and then recrystallized from ether to obtain the titled compound (0.077 g, 0.144 mmol, 27percent). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 90℃; for 16.0h;Product distribution / selectivity; | A.5 (5-Chloro-[l, 2, 4]triazolo[l, 5-a]pyridin-8-yl)-(4-morpholin-4-yl-phenyl)-amine[0332] A suspension of 8-bromo-5-chloro-[l,2,4]triazolo[l,5-a]pyridine (160 mg, 0.69 mmol),4-morpholin-4-yl-phenylamine (135 mg, 0.76 mmol), sodium-tert-butoxide (93 mg, 0.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 13.76 mumol) and Xantphos (16 mg, 27.52 mumol) in dry toluene is heated at 90 0C in a sealed tube under a nitrogen atmosphere for 16 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and 10 % aqueous citric acid. The organic phase is further washed with water (Ix) and brine (Ix), dried over magnesium sulfate, filtered and evaporated. The solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3) affording the title compound (70 mg) as a solid. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | With toluene-4-sulfonic acid; In 1,4-dioxane;Heating / reflux; | A mixture of <strong>[499195-60-7]ethyl 4-(2-chloropyrimidin-4-yl)benzoate</strong> (26.15 g, 99.7 mmol) and 4-morpholinoaniline (23.10 g, 129.6 mmol) was suspended in 1,4-dioxane (250 mL). p- Toluenesulfonic acid monohydrate (17.07 g, 89.73 mmol) was added. The mixture was heated at reflux for 40 h., cooled to ambient temperature, concentrated then the residue was partitioned between ethyl acetate and 1 : 1 saturated sodium bicarbonate/water (IL total). The organic phase was washed with water (2 x 100 mL) and concentrated. The aqueous phase was extracted with dichloromethane (3 x 200 mL). The material which precipitated during this workup was collected by filtration and set aside. The liquid organics were combined, concentrated, triturated with methanol (200 mL) and filtered to yield additional yellow solid. The solids were combined, suspended in methanol (500 mL), allowed to stand overnight then sonicated and filtered. The solids were washed with methanol (2x 50 mL) to give, after drying, ethyl 4-(2-(4- morphonlinophenylamino)pyrimidin-4-yl)benzoate (35.39 g , 88%). 1H NMR (300 MHz, J6-DMSO) delta 9.49 (IH, s); 8.54 (IH, d, J= 5.0 Hz); 8.27 (2H, d, J= 8.7 Hz); 8.10 (2H, d, J= 8.7 Hz), 7.66 (2H, d, J= 9.1 Hz); 7.38 (IH, d, J= 5.0Hz); 6.93 (2H, d, J= 8.7 Hz); 4.35 (2H, q, J= 6.9 Hz), 3.73 (4H, m); 3.04 (4H, m); 1.34 (3H, t, J= 6.9 Hz); LC-ESI- MS (method B): rt 7.5 min.; m/z 404.1 [M+H]+. |
[ 2524-67-6 ]
[ 76661-24-0 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80.4% | With trifluoroacetic acid; In iso-butanol; at 100℃; | General procedure: To a solution of 3a-r (1.50 mmol, 1 eq) and 6a-b (1.50 mmol, 1eq) in 2-BuOH (8 mL) were added TFA (2 mL). The slurrywas heatedto 100 C for 2e3 h. The reaction mixture was allowed to cool toroom temperature and was neutralized with a saturated aqueoussodium bicarbonate solution. The mixture was then extracted withethyl acetate (50 mL) three times. The crude was purified by flashchromatography with 25:1 (v/v) dichloromethane - methanol. |

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