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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
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Structure of 7152-15-0
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 7152-15-0 |
Formula : | C8H14O3 |
M.W : | 158.20 |
SMILES Code : | C(=O)(CC(=O)C(C)C)OCC |
MDL No. : | MFCD00009198 |
InChI Key : | XCLDSQRVMMXWMS-UHFFFAOYSA-N |
Pubchem ID : | 81583 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225 |
Precautionary Statements: | P210-P403+P235 |
Class: | 3 |
UN#: | 3272 |
Packing Group: | Ⅲ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.75 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 42.05 |
TPSA ? Topological Polar Surface Area: Calculated from |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.92 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.16 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.97 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.38 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.35 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.3 |
Solubility | 7.86 mg/ml ; 0.0497 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.8 |
Solubility | 2.5 mg/ml ; 0.0158 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.52 |
Solubility | 4.72 mg/ml ; 0.0299 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) |
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 |
-6.35 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 |
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) |
1.71 |
* 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 |
---|---|---|
51.3% | With sodium acetate; acetic acid; In water; | (1) Ethyl 4-(4-fluorophenyl)-2-isopropylpyrrole-3-carboxylate 1 STR6 A mixture of 6.85 g (43.3 mmol) of ethyl isobutyrylacetate, 10.69 g (56.3 mmol) of 2-amino-4'-fluoracetophenone hydrochloride, 16.3 ml of acetic acid, 6.04 g of sodium acetate, and 10.8 ml of water is refluxed for 4 hours. After cooling, the reaction mixture is adjusted to pH 8 with saturated NaHCO3 and extracted with ether. The extract, 8.36 g, is subjected to column chromatography with silica gel, eluding with methylene chloride to give 6.12 g (Yield:51.3%) of the compound 1. NMR (CDCl3) delta: 1.14 (t, 3H, J=7 Hz); 1.31 (d, 6H, J=7 Hz); 3.81 (septet, 1H, J=7 Hz); 4.15 (q, 2H, J=7 Hz); 6.58 (d, 1H, J=2,4 Hz); 6.96-7.05 (m, 2H); 7.29-7.37 (m, 2H); 8.36 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With sulfuric acid; at 0 - 20℃; | To the mixture of compound 1 (3.0 g, 21.0 mmol) and compound 2 (4.0 g, 25.0 mmol), H2SO4(9 mL) was added slowly at 0 C. The mixture was stirred at RT overnight. The reaction mixture was poured into H2O (10 mL) and stirred for 30 mins, the formed precipitate was filtered and washed with water, dried to give compound 3 (2.0 g, 41% yield) as light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With triethylamine; In ethanol; N,N-dimethyl acetamide; at 20 - 100℃; for 2h; | Taking 25 ml round-bottom flask, the intermediate isobutyryl ethyl acetate (1.33g, 8 . 39mmol) dissolved in 11mLN, dipropylene N-dimethyl formamide methanol 100 C stirring overnight. After the reaction is distilled under reduced pressure to obtain crude products. The intermediate is dissolved in 11 ml of ethanol, add 1.1 ml triethylamine, <strong>[658-27-5]3-fluorophenylhydrazine</strong> hydrochloride compound (1.36g, 8 . 39mmol), the reaction room temperature for 2 hours. After the reaction, by adding 150 ml water, ethyl acetate extraction three times (50mLx3), combined with the phase, saturated salt water washing three times (50mLx3), anhydrous sodium sulfate for drying; concentrated, dry sample, rapid preparation of chromatographic silica gel column (ethyl acetate: petroleum ether = 30:1) separated to obtain oily liquid 832 mg, yield 36%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With polyphosphoric acid; at 120℃; for 2.0h; | To a solution of 6-chioro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (5 mL) was added ethyl 4-methyl-3-oxo-pentanoate (1.13 mL}. The mixture was heated to 85 C for 1 hour, then 120 C for 1 hour. While still hot, the mixture was slowly added to a stirred solution of saturated aqueous NaHCOg (150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes and the organic layer was isolated. The aqueous layer was further extracted with chloroform/IPA (4:1) (3 x 50 L) and the organic layers were pooled, dried over MgSC , filtered, and concentrated. The crude product was purified using a Teledyne I5CO Combi-Flash system (liquid loading with DCM, 80G column, 0 - 65% EtOAc/Hex, 20 min run). The column was then flushed with hexanes followed by 0 - 2% MeOH/DCM, 10 min to give the title compound (204 mg; 23% yield) as a solid. : NMR (400 MHz, CDCI3) d 6.47 (s, 1H), 3.63 (hept, J = 6.8 Hz, 1H), 2.56 (d, 1 = 1.0 Hz, 3H), 2.44 (d, J = 1.0 Hz, 3H), 1.32 (s, 3H), 1.30 (s, 3H). ES-MS [M+l]+: 252. |
23% | With polyphosphoric acid; at 120℃; for 2.0h; | To a solution of 6-chioro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (5 mL) was added ethyl 4-methyl-3-oxo-pentanoate (1.13 mL}. The mixture was heated to 85 C for 1 hour, then 120 C for 1 hour. While still hot, the mixture was slowly added to a stirred solution of saturated aqueous NaHCOg (150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes and the organic layer was isolated. The aqueous layer was further extracted with chloroform/IPA (4:1) (3 x 50 L) and the organic layers were pooled, dried over MgSC , filtered, and concentrated. The crude product was purified using a Teledyne I5CO Combi-Flash system (liquid loading with DCM, 80G column, 0 - 65% EtOAc/Hex, 20 min run). The column was then flushed with hexanes followed by 0 - 2% MeOH/DCM, 10 min to give the title compound (204 mg; 23% yield) as a solid. : NMR (400 MHz, CDCI3) d 6.47 (s, 1H), 3.63 (hept, J = 6.8 Hz, 1H), 2.56 (d, 1 = 1.0 Hz, 3H), 2.44 (d, J = 1.0 Hz, 3H), 1.32 (s, 3H), 1.30 (s, 3H). ES-MS [M+l]+: 252. |
23% | With polyphosphoric acid; at 120℃; for 2.0h; | To a solution of 6-chioro-3-amino-4,5-dimethylpyridazine (550 mg) in polyphosphoric acid (5 mL) was added ethyl 4-methyl-3-oxo-pentanoate (1.13 mL}. The mixture was heated to 85 C for 1 hour, then 120 C for 1 hour. While still hot, the mixture was slowly added to a stirred solution of saturated aqueous NaHCOg (150 mL) and chloroform/IPA (4:1) (50 mL). Upon complete addition, the mixture was stirred for 10 minutes and the organic layer was isolated. The aqueous layer was further extracted with chloroform/IPA (4:1) (3 x 50 L) and the organic layers were pooled, dried over MgSC , filtered, and concentrated. The crude product was purified using a Teledyne I5CO Combi-Flash system (liquid loading with DCM, 80G column, 0 - 65% EtOAc/Hex, 20 min run). The column was then flushed with hexanes followed by 0 - 2% MeOH/DCM, 10 min to give the title compound (204 mg; 23% yield) as a solid. : NMR (400 MHz, CDCI3) d 6.47 (s, 1H), 3.63 (hept, J = 6.8 Hz, 1H), 2.56 (d, 1 = 1.0 Hz, 3H), 2.44 (d, J = 1.0 Hz, 3H), 1.32 (s, 3H), 1.30 (s, 3H). ES-MS [M+l]+: 252. |
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