Structure of 112006-57-2
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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. : | 112006-57-2 |
Formula : | C15H16N2OS |
M.W : | 272.37 |
SMILES Code : | O=C(N(C)C)C1=C(SCC2=CC=CC=C2)N=CC=C1 |
MDL No. : | MFCD08316155 |
InChI Key : | MPGOCEUHZWEFJX-UHFFFAOYSA-N |
Pubchem ID : | 11086903 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 19 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 78.34 |
TPSA ? Topological Polar Surface Area: Calculated from |
58.5 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.23 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.65 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.92 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.26 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.92 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.6 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.34 |
Solubility | 0.126 mg/ml ; 0.000462 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.53 |
Solubility | 0.0805 mg/ml ; 0.000295 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.12 |
Solubility | 0.00208 mg/ml ; 0.00000764 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) |
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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-6.08 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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.5 |
* 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 |
---|---|---|
In N-methyl-acetamide; water; | EXAMPLE 1 N,N-Dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide A solution of 25.0 g (223 mmol) of potassium t-butoxide in 100 ml of dimethylformamide was cooled to 0 C. and 22 ml (186 mmol) of benzyl mercaptan added dropwise at 0 C. After addition was complete, the reaction mixture was allowed to warm to 25 C. and stirred at this temperature for 15 minutes. The reaction mixture was then re-cooled to O C. and 34.0 g (186 mmol) of N,N-dimethyl-2-(chloro)-3-pyridinecarboxamide added in one portion. After an exotherm to 50 C., the mixture was heated at 80 C. for 1.5 hour. The mixture was cooled, poured into 100 ml of water and extracted with ether. The combined organic extracts were washed twice with water, then brine and dried over sodium sulfate. Concentration gave 19.2 g of a viscous yellow oil. IR (Nujol) 1640 (CONMe2) cm-1. NMR (CDCl3): delta2.72 (s, 3H, NCH3); 3.04 (s, 3H, NCH3); 4.49 (s, 2H, SCH2 C6 H5); 6.97-7.17 (m, 1H); 7.18-7.57 (m, 6H); and 8.50 (d of d, 1H). | |
In N-methyl-acetamide; water; | EXAMPLE 1 N,N-Dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide A solution of 25.0 g (223 mmol) of potassium t-butoxide in 100 ml of dimethylformamide was cooled to 0 C. and 22 ml (186 mmol) of benzyl mercaptan added dropwise at 0 C. After addition was complete, the reaction mixture was allowed to warm to 25 C. and stirred at this temperature for 15 minutes. The reaction mixture was then re-cooled to 0 C. and 34.0 g (186 mmol) of N,N-dimethyl-2-(chloro)-3-pyridinecarboxamide added in one portion. After an exotherm to 50 C., the mixture was heated at 80 C. for 1.5 hour. The mixture was cooled, poured into 100 ml of water and extracted with ether. The combined organic extracts were washed twice with water, then brine and dried over sodium sulfate. Concentration gave 19.2 g of a viscous yellow oil. IR (Nujol) 1640 (CONMe2) cm-1. NMR (CDCl3): delta 2.72 (s, 3H, NCH3); 3.04 (s, 3H, NCH3); 4.49 (s, 2H, SCH2 C6 H5); 6.97-7.17 (m, 1H); 7.18-7.57 (m, 6H); and 8.50 (d of d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hypochlorite; ammonia; In dichloromethane; water; | EXAMPLE 2 N,N-Dimethyl-2-aminosulfonyl-3-pyridinecarboxamide A mixture of 4.4 ml of concentrated hydrochloric acid, 66 ml of methylene chloride, 34 ml of water and 4.0 g (14.7 mmol) of the <strong>[112006-57-2]N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide</strong> was cooled to 0 C. Maintaining a temperature of -5 to 3 C., 60 ml (40.5 mmol) of 5% sodium hypochlorite was added dropwise over 15 minutes. The resulting yellow emulsion was stirred at 0 C. an additional 20 minutes. The reaction mixture was then poured into water and extracted with methylene chloride. The combined organic extracts were kept at 0 C. and washed with a saturated sodium bisulfite solution and dried over sodium sulfate. After 30 minutes, the yellow solution was filtered into a reaction flask and cooled to -78 C. and 5 ml (431 mmol) of dry ammonia added. The reaction mixture was allowed to warm to room temperature and the solvent removed under reduced pressure. The resulting solid was slurried with 5 ml of water and the insoluble white solid collected by filtration to provide 2.0 g of the subject compound, m.p. 198-209 C.(d). NMR (DMSO): delta 2.70 (s, 3H, NCH3); 2.93 (s, 3H, NCH3); 7.60-7.75 (m, 1H); 7.90 (m, 1H); and 8.75 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.1 parts (93.9%) | With thionyl chloride; dimethyl amine; In water; ethyl acetate; | EXAMPLE 5 N,N-Dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide A mixture of 29.7 parts of thionylchloride, 50.0 parts of 2-(phenylmethylthio)-3-pyridinecarboxylic acid, and 225 parts of ethyl acetate was refluxed for 1.6 hours. The resulting solution of 2-(phenylmethylthio)-3-pyridinecarbonyl chloride was cooled to 5 C. While maintaining the temperature at approximately 10 C., 70 parts of 40% dimethylamine in water were added. The pH was adjusted to 4.0 with 36% HCl and the lower aqueous layer was decanted. Water was added to the ethyl acetate layer and the resulting mixture was distilled until the ethyl acetate was removed. After cooling and seeding, N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide was recovered by filtration, washed with water, and dried. This gave 52.1 parts (93.9%), melting point 61-63 C. |
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