Structure of 126764-17-8
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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. : | 126764-17-8 |
| Formula : | C9H13Cl |
| M.W : | 156.65 |
| SMILES Code : | CC(C)(C#CC=CCCl)C |
| MDL No. : | MFCD04039160 |
| InChI Key : | ZIXABMZBMHDFEZ-GQCTYLIASA-N |
| Pubchem ID : | 11389521 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P302+P352-P305+P351+P338-P321-P405-P501 |
| Num. heavy atoms | 10 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.56 |
| Num. rotatable bonds | 1 |
| Num. H-bond acceptors | 0.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 47.6 |
| TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.87 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.39 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.91 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.66 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.87 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.14 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.88 |
| Solubility | 0.206 mg/ml ; 0.00132 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.07 |
| Solubility | 0.134 mg/ml ; 0.000853 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.27 |
| Solubility | 0.841 mg/ml ; 0.00537 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
| 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) |
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 |
-4.85 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 |
2.0 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) |
3.72 |
* 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 |
|---|---|---|
| 29 kg of N-methyl-1 -naphthalene methylamine hydrochloride was charged into a reactor containing 70.4 liters of dimethylformamide and 11 liters of water, under stirring. The contents were stirred for 15 minutes for clear dissolution and 11 kg of sodium carbonate was added to it. The reaction mass was cooled to 13 EPO <DP n="18"/>C and 22 kg of 1-chloro-6,6-dimethyl-2-heptene-4-yne was added slowly at 11 to 14 C. The reaction mixture was stirred at 12 to 14 0C for 60 minutes and then heated to 55 0C. The reaction mass was maintained at 60 C for 5 hours and reaction completion was confirmed by thin layer chromatography. The reaction mass was cooled to room temperature and 99 liters of water was added. Reaction mass was extracted three times with a total of 75 liters of dichloromethane (3x25 liters). Total organic layer was washed twice with 88 liters of water (2x44 liters); 18 liters of water was charged to the final organic layer and was cooled to 13 0C. Reaction mass pH was adjusted to 0.2 by adding 15 liters of 36% aqueous hydrochloric acid and stirring for 30 minutes. The organic layer was separated and washed three times with a total of 267 liters of water (3chi89 liters). Final organic layer was transferred into a reactor and the solvent was distilled completely below 45 C. 11.8 liters of petroleum ether was charged and the solvent distilled completely at below 50 C. Again 68 liters of petroleum ether was charged and heated to reflux. The mass was stirred at reflux for 30 minutes and cooled to 50 C. The solid thus formed was allowed to settle for 60 minutes and the top petroleum ether layer was decanted. The decantation process was repeated two more times. Finally 44 liters of petroleum ether was charged, heated to reflux, maintained for 30 minutes at reflux and then cooled to 25 C. The contents were stirred for 60 minutes at 20 to 25 0C and centrifuged to recover the solid. The centrifuged solid was washed twice with petroleum ether (2x16 liters) and spin- dried for about 60 minutes to get 29.3 kg of crude terbinafine hydrochloride as a semi-dry solid. | ||
| Example-3: Preparation of Terbinafine hydrochloride compound of formula- 160 grams of sodium carbonate is added to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water and 100 ml of dimethyl formamide at an ambient temperature. Stirred the reaction mixture for 45 minutes at ambient temperature. Cooled the mixture to 10-15C and slowly added 34 grams of 6,6-dimethyl-l-chlorohept-2-ene-4-yne. Heated the reaction mixture to 70-750C and stirred for 6 hours. Cooled the reaction mixture to 25-350C. Decomposed the reaction mixture with water. Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed the organic phase thrice with water. Separated the organic phase and added water then cooled to 10-150C. Slowly added 160.5 ml of hydrochloric acid. Stirred for 30 minutes. Separated the organic phase and washed with water. Distilled the organic phase completely under reduced pressure at below 500C. Hexanes added to the obtained crude and decanted thrice. Isolated the title compound using acetone. The obtained compound purified using acetonitrile as a solvent. Yield 75 grams.Example-4: Preparation of Terbinafine hydrochloride compound of formula- 160 grams of sodium carbonate is added to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water and 100 ml of dimethylformamide at an ambient temperature. Stirred the reaction mixture for 45 minutes at ambient temperature. Cooled the mixture to 10-150C and slowly added 112.5 grams of 6,6-dimethyl-l-chlorohept-2-ene-4-yne. Heated the reaction mixture to 70-750C and stirred for 6 hours. Cooled the reaction mixture to 25-35C. Decomposed the reaction mixture with water. Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed the organic phase thrice with water. Separated the organic phase and added water then cooled to 10-150C. Slowly added 160.5 ml hydrochloric acid. Stirred for 30 minutes. Separated the organic phase and washed with water. Distilled the organic phase completely under reduced pressure at below 500C. Isolated the compound using acetone. The obtained compound purified using acetonitrile as a solvent. Yield 75 grams | ||
| Example-5: Preparation of Terbinafine hydrochloride compound of formula- 160 grams of sodium carbonate is added to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water at an ambient temperature. Stirred the reaction mixture for 45 minutes at ambient temperature. Cooled the mixture to 10-15C and slowly added 112.5 grams of 6,6-dimethyl-l-chlorohept-2-ene-4-yne. Heated the reaction mixture to 70-75C and stirred for 6 hours. Cooled the reaction mixture to 25-350C. Decomposed the reaction mixture with water. Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed the organic phase thrice with water. Separated the organic phase and added water then cooled to 10-15C. Slowly added 160.5 ml hydrochloric acid. Stirred for 30 minutes. Separated the organic phase and washed with water. Distilled the organic phase completely under reduced pressure at below 5O0C. Isolated the compound using acetone. The obtained compound purified using acetonitrile as a solvent. Yield 75 grams |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium carbonate; In water; at 10 - 75℃; for 6.75h;Product distribution / selectivity; | Example-6: Preparation of crystalline Form-I of Terbinafine compound of formula-3 Added 60 grams of sodium carbonate to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water and at an ambient temperature. Stirred the reaction mixture for 45 minutes at an ambient temperature. Cooled the reaction mixture to 10-150C. Added 112.5 grams of 6,6-dimethyl-l-chlorohept-2-ene-4-yne to the above reaction mixture at 10-15C. Heated the reaction mixture to 70-750C. Stirred the reaction mixture for 6 hours at 70-750C. Cooled the reaction mixture to 25-35C. Quenched the reaction mixture with water. Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed thrice with water. Separated the organic phase. Distilled the organic phase completely under reduced pressure at below 500C. Added 50 ml of isopropyl alcohol to the above reaction mixture. Distilled the solvent completely under reduced pressure at below 500C. Cooled the reaction mixture to 25-350C. Added 180 ml of isopropyl alcohol to the above reaction mixture and heated to reflux. Stirred the reaction mixture at reflux for 20 minutes. Cooled the reaction mixture to 0-50C. Stirred the reaction mixture for 60 minutes at 0-50C. Filtered the <n="24"/>precipitated solid and washed with chilled isopropyl alcohol. Dried the material to get the crystalline Form-I of Terbinafme. Yield: 74 grams | |
| With sodium carbonate; In water; N,N-dimethyl-formamide; at 10 - 75℃; for 6.75h;Product distribution / selectivity; | Example-7: Preparation of crystalline Form-I of Terbinafine compound of formula-3Added 60 grams of sodium carbonate to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water and of dimethylformamide at an ambient temperature. Stirred the reaction mixture for 45 minutes at an ambient temperature. Cooled the reaction mixture to 10-15C. Added 112.5 grams of 6,6-dimethyl- l-chlorohept-2-ene-4-yne to the above reaction mixture at 10-15C. Heated the reaction mixture to 70-75C. Stirred the reaction mixture for 6 hours at 70-75C. Cooled the reaction mixture to 25-35C. Quenched the reaction mixture with water. Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed thrice with water. Separated the organic phase. Distilled the organic phase completely under reduced pressure at below 5O0C. Added 50 ml of ethyl acetate to the above reaction mixture. Distilled the solvent completely under reduced pressure at below 60C. Cooled the reaction mixture to 25-35C. Added 180 ml of ethyl acetate to the above reaction mixture and heated to reflux. Stirred the reaction mixture at reflux for 20 minutes. Cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 60 minutes at 0-5C. Filtered the precipitated solid and washed with chilled ethyl acetate. Dried the material to get the crystalline Form-I of Terbinafine. Yield: 72 gramsExampIe-8: Preparation of crystalline Form-I of Terbinafine compound of formula-3 Added 60 grams of sodium carbonate to a solution of 75 grams of N-methyl naphthylmethyl amine hydrochloride in 450 ml of water and 100 ml of dimethyl formamide at an ambient temperature. Stirred the reaction mixture for 45 minutes at an ambient temperature. Cooled the reaction mixture to 10-150C. Added 112.5 grams of 6,6-dimethyl-l-chlorohept-2-ene-4-yne to the above reaction mixture at 10-150C. Heated the reaction mixture to 70-75C. Stirred the reaction mixture for 6 hours at 70-750C. Cooled the reaction mixture to 25-350C. Quenched the reaction mixture with water. <n="25"/>Extracted the reaction mixture thrice with methylene chloride. Combined all the organic phases and washed thrice with water. Separated the organic phase. Distilled the organic phase completely under reduced pressure at below 50C. Added 50 ml of acetone to the above reaction mixture. Distilled the solvent completely under reduced pressure at below 60C. Cooled the reaction mixture to 25-35C. Added 180 ml of acetone to the above reaction mixture and heated to reflux. Stirred the reaction mixture at reflux for 20 minutes. Cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 60 minutes at 0-5C. Filtered the precipitated solid and washed with chilled acetone. Dried the material to get the crystalline Form-I of Terbinafme. Yield: 73 grams |
Tags: 126764-17-8 synthesis path| 126764-17-8 SDS| 126764-17-8 COA| 126764-17-8 purity| 126764-17-8 application| 126764-17-8 NMR| 126764-17-8 COA| 126764-17-8 structure

A1148064 [287471-30-1]
(E)-1-Chloro-6,6-dimethylhept-2-en-4-yne
Similarity: 1.00
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| H335 | May cause respiratory irritation |
| H336 | May cause drowsiness or dizziness |
| H340 | May cause genetic defects |
| H341 | Suspected of causing genetic defects |
| H350 | May cause cancer |
| H351 | Suspected of causing cancer |
| H360 | May damage fertility or the unborn child |
| H361 | Suspected of damaging fertility or the unborn child |
| H361d | Suspected of damaging the unborn child |
| H362 | May cause harm to breast-fed children |
| H370 | Causes damage to organs |
| H371 | May cause damage to organs |
| H372 | Causes damage to organs through prolonged or repeated exposure |
| H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
| Code | Phrase |
| H400 | Very toxic to aquatic life |
| H401 | Toxic to aquatic life |
| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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