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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
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Structure of 6290-17-1
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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'.
Search for reports by entering the product batch number.
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CAS No. : | 6290-17-1 |
Formula : | C9H16O4 |
M.W : | 188.22 |
SMILES Code : | CC1(OCC(O1)C)CC(OCC)=O |
MDL No. : | MFCD00151819 |
InChI Key : | GSIXJEIRJVOUFB-UHFFFAOYSA-N |
Pubchem ID : | 95392 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.89 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.76 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.48 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.68 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.55 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.27 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.17 |
Solubility | 12.7 mg/ml ; 0.0674 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.2 |
Solubility | 12.0 mg/ml ; 0.0636 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.61 |
Solubility | 4.6 mg/ml ; 0.0244 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 |
-6.97 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 |
0.0 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) |
3.27 |
* 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 |
---|---|---|
Example 26 (Comparative): Adaptation of the process by Ueda et al. 1982 for the preparation of the compound of formula (VII)/(VIIa) 5-methyl-l-(naphthalen-2-yl)-lH- pyrazol-3-olNaphthalen-2-ylhydrazine hydrochloride (30 g) and NaOMe (20,85 g) were slurried in toluene (300 ml) and heated to 80/85 °C. Ethyl 2-(2,4-dimethyl-l,3-dioxolan-2- yl)acetate (30,6 ml) was added and maintained for 90 min. Ethyl 2-(2,4-dimethyl-l,3- dioxolan-2-yl)acetate (8,2 ml) and NaOMe (2,5 g) were added and maintained for 2 h. NaOMe (1,7 g) was added and maintained for 1 h. The mixture was cooled to room temperature, water (450 ml) was added and pH adjusted to 6-8 with aqueous HC1. The organic layer was concentrated to dryness under vacuum and methanol (450 ml), HC1 35percent (18 ml) and water (54 ml) were added. The mixture was heated to reflux for 90 min and concentrated under vacuum to 165 ml of final volume. Water (120 ml) and CH2C12 (120 ml) were added and pH adjusted to 12,2-12,7 (basified with NaOH 25percent). Upper organic layer was discarded, and pH of lower aqueous layer was adjusted to 5,0- 7,0 with acetic acid 80percent. The solid was filtered, washed with water (45 ml) and slurried in ethyl acetate (102 ml) 2 h at 20/25 °C. The solid was filtered, washed with ethyl acetate (15 ml) and dried to yield 20,24 g (46percent) of a mixture [5-methyl-l- (naphthalen-2-yl)-lH-pyrazol-3-ol]: [3-methyl-l-(naphthalen-2-yl)-lH-pyrazol-5-ol] (80:20). | ||
Example 26Adaptation of the process by Ueda et al.1982 for the preparation of 5-methyl-1-(naphthalen-2-yl)-1H -pyrazol-3-olNaphthalen-2-ylhydrazine hydrochloride (30 g) and NaOMe (20,85 g) were slurried in toluene (300 ml) and heated to 80/85 °C. Ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate (30,6 ml) was added and maintained for 90 min.Ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate (8,2 ml) and NaOMe (2,5 g) were added and maintained for 2 h. NaOMe (1,7 g) was added and maintained for 1 h.The mixture was cooled to room temperature, water (450 ml) was added and pH adjusted to 6-8 with aqueous HCl.The organic layer was concentrated to dryness under vacuum and methanol (450 ml), HCl 35percent (18 ml) and water (54 ml) were added.The mixture was heated to reflux for 90 min and concentrated under vacuum to 165 ml of final volume.Water (120 ml) and CH2Cl2 (120 ml) were added and pH adjusted to 12,2-12,7 (basified with NaOH 25percent).Upper organic layer was discarded, and pH of lower aqueous layer was adjusted to 5,0-7,0 with acetic acid 80percent.The solid was filtered, washed with water (45 ml) and slurried in ethyl acetate (102 ml) 2 h at 20/25 °C.The solid was filtered, washed with ethyl acetate (15 ml) and dried to yield 20,24 g (46percent) of a mixture [5-methyl-1-(naphthalen-2-yl)-1H-pyrazol-3-ol]: [3-methyl-1-(naphthalen-2-yl)-1H-pyrazol-5-ol] (80:20). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Example 1 : Preparation of 2-(2,4-dimethyl-L3-dioxolan-2-yl)acetic acid [compoundThe acid 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetic acid was obtained as a derivative from saponification of the ester ethyl 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetate. The hydrolysis of ethyl 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetate in alkaline medium is described in different publications: a) Miranda et al, Tetrahedron, 1987, 143; b) Lelandais et al, Can. J. Chem., 1983, 584; c) Oku et al., J. Org. Chem., 1997, 2123. The acid was obtained with variable yields 50-82percent.3.6 g of ethyl 2-(2,4-dimethyl-l,3-dioxolan-2-yl)acetate in a solution of 1.18 g (1.1 equiv.) of KOH in 8 mL of water were mixed at room temperature under magnetic stirring. After 4 h, the basic aqueous layer was removed with 5 mL of tert-butyl methyl ether, recovering 257 mg (7percent) from the starting material. The aqueous layer was brought to dryness. The residue was stirred in a mixture with 2 ml NaCl-saturated water and 8 mL of CH2CI2 under vigorous stirring. H2SO4 were added until achieving an acidic pH. The organic layers were dried with sodium sulphate, filtered off and evaporated obtaining 2.344 g of the title compound (82percent considering the previously recovered 7percent). | |
82% | Example 1Preparation of 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetic acidThe acid 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetic acid was obtained as a derivative from saponification of the ester <strong>[6290-17-1]ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate</strong>.The hydrolysis of <strong>[6290-17-1]ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate</strong> in alkaline medium is described in different publications: a) ; b) ; c) .The acid was obtained with variable yields 50-82percent.3.6 g of <strong>[6290-17-1]ethyl 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetate</strong> in a solution of 1.18 g (1.1 equiv.) of KOH in 8 mL of water were mixed at room temperature under magnetic stirring.After 4 h, the basic aqueous layer was removed with 5 mL of tert-butyl methyl ether, recovering 257 mg (7percent) from the starting material.The aqueous layer was brought to dryness.The residue was stirred in a mixture with 2 ml NaCl-saturated water and 8 mL of CH2Cl2 under vigorous stirring.H2SO4 were added until achieving an acidic pH.The organic layers were dried with sodium sulphate, filtered off and evaporated obtaining 2.344 g of the title compound (82percent considering the previously recovered 7percent). |