Structure of 6310-21-0
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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. : | 6310-21-0 |
Formula : | C10H15N |
M.W : | 149.23 |
SMILES Code : | NC1=CC=CC=C1C(C)(C)C |
MDL No. : | MFCD00130023 |
InChI Key : | AEIOZWYBDBVCGW-UHFFFAOYSA-N |
Pubchem ID : | 80574 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 50.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.09 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.98 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.57 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.76 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.53 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.98 |
Solubility | 0.156 mg/ml ; 0.00105 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.19 |
Solubility | 0.0964 mg/ml ; 0.000646 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.23 |
Solubility | 0.0881 mg/ml ; 0.00059 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 |
-5.09 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 |
2.0 |
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) |
1.0 |
* 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 |
---|---|---|
59% | 2-t-Butylaniline (13.35 g, 89.4 mmol) was diazotized in sulfuric acid (25% w/w, 110 mL) with sodium nitrite (9.34 g) in water (18 mL) at -20 C. The diazonium salt was transferred to a solution of potassium iodide (67 g) in water 20 mL, and after 18 hours, a solution of sodium hydroxide (25 g) in water (100 mL) was added. The mixture was extracted with hexanes, hexane extracts passed through a column of silica gel, and concentrated. The product was obtained as a liquid, 13.77 g (59%). Mass spec: m/z 260 (M+). 1H NMR (CDCl3) δ ppm: 1.53 (s, 9H), 6.82 (td, 1H, 1.68 and 7.68 Hz), 7.27 (td, 1H, 1.4 and 7.32 Hz), 7.43 (dd, 1H, 1.64 and 8.0 Hz), 7.99 (dd, 1.4 and 7.8 Hz). | |
45% | With toluene-4-sulfonic acid; potassium iodide; sodium nitrite; In water; tert-butyl alcohol; at -3 - 20℃; for 17.5h; | 28.7g (151mmol) of p-toluenesulfonic acid monohydrate were dissolved in 75ml of tert- butanol.5.0g (33.5mmol) of 2-(tert-butyl)aniline were added, and the final white suspension was cooled to -3C. A solution of 6.93g (101mmol) of sodium nitrite and 20.86g (126mmol) of potassium iodide in 30ml of water was added within 30 minutes. It was warmed up to room temperature and stirred for 17 hours.27.4g (174mmol) of sodium sulfurothioate were dissolved in 100ml of water and added to the reaction mixture.11.26g (134mmol) of sodium bicarbonate were dissolved in 100ml of water and added, then the mixture was stirred for 30 minutes. The reaction mixture was diluted with 200ml of cyclohexane, the phases were separated and the water phase was extracted with cyclohexane. The combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by column chromatography (heptane/ethyl acetate) to give 5.36g (45% yield) of Intermediate 47-1. 1H NMR (400 MHz, Methylene Chloride-d2) d 8.00 (dd, J = 7.8, 1.5 Hz, 1H), 7.46 (dd, J = 8.0, 1.7 Hz, 1H), 7.36- 7.23 (m, 1H), 6.89- 6.78 (m, 1H), 1.54 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With EDAC; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; | EXAMPLE 154 Step A-Preparation of N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide A solution of <strong>[171178-50-0]2,6-difluoropyridine-3-carboxylic acid</strong> (3.2 g, 20 mmol), t-butylaniline (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmol), and DIEA (8 mL) in CH2Cl2 (80 mL) was stirred at RT for 1 h. The mixture was washed with aq. NaHCO3 and brine. The organic solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica (Hex:EtOAc=4:1) to give a light yellow flaky crystal as desired product. | |
With EDAC; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; | Step A-Preparation of N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide A solution of <strong>[171178-50-0]2,6-difluoropyridine-3-carboxylic acid</strong> (3.2 g, 20 mmol), t-butylaniline (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmol), and DIEA (8 mL) in CH2Cl2 (80 mL) was stirred at RT for 1 h. The mixture was washed with aq. NaHCO3 and brine. The organic solution was dried over Na2SO4 and concentrated in vacuo The residue was purified via flash chromatography on silica (Hex:EtOAc=4:1) to give a light yellow flaky crystal as desired product. | |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1h; | Step A-Preparation of N-(4-tert-butyl-phenyl)-2,6-difluoro-nicotinamide A solution of <strong>[171178-50-0]2,6-difluoropyridine-3-carboxylic acid</strong> (3.2 g, 20 mmol), t-butylaniline (3.0 g, 20 mmol), HOBt (2.6 g, 20 mmol), EDAC (8 g, 40 mmol), and DIEA (8 mL) in CH2Cl2 (80 mL) was stirred at RT for 1 h.The mixture was washed with aq. NaHCO3 and brine.The organic solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified via flash chromatography on silica (Hex:EtOAc=4:1) to give a light yellow flaky crystal as desired product. |
A114084 [42014-60-8]
4-(tert-Butyl)-2,6-dimethylaniline
Similarity: 0.94
A114084 [42014-60-8]
4-(tert-Butyl)-2,6-dimethylaniline
Similarity: 0.94