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Structure of Sulpiride impurity A
CAS No.: 26116-12-1
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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. : | 26116-12-1 |
Formula : | C7H16N2 |
M.W : | 128.22 |
SMILES Code : | CCN1CCCC1CN |
MDL No. : | MFCD00003178 |
InChI Key : | UNRBEYYLYRXYCG-UHFFFAOYSA-N |
Pubchem ID : | 117295 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 3(8) |
UN#: | 2733 |
Packing Group: | Ⅲ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.17 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.96 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.24 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.05 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.57 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.57 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.65 |
Solubility | 28.4 mg/ml ; 0.222 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.41 |
Solubility | 49.3 mg/ml ; 0.385 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.89 |
Solubility | 16.4 mg/ml ; 0.128 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 |
No |
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 |
-6.91 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) |
1.51 |
* 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 |
---|---|---|
61% | With triethylamine; In water; acetone; | N-(1-ethyl 2-pyrrolidylmethyl) 2-methoxy 4-amino 5-ethylsulphonyl benzamide 81 g of <strong>[71675-87-1]2-methoxy 4-amino 5-ethylsulphonyl benzoic acid</strong> and 297 cm3 of acetone are placed in a flask fitted with an agitator, a thermometer and a dropping funnel, followed by 33 g of triethylamine. The solution is cooled to 0° C., then 30 g of ethyl chloroformate is added drop by drop between 0° and 5° C. When the mixture has been agitated 51 g of 1-ethyl 2-amino methyl pyrrolidine is added drop by drop between 5° and 10° C. The mixture is agitated at 10° C. then at ambient temperature. The triethylamine hydrochloride which precipitates is drained, then the acetone is distilled. The residue is dissolved in 600 cm3 of water in the presence of caustic soda solution. The base crystallises after seeding and is drained, washed with water and dried. When the crystals have been purified by passing them through hydrochloride and re-crystallising them in acetone, 66 g of N-[1-ethyl 2-pyrrolidylmethyl] 2-methoxy 4-amino 5-ethylsulphonyl benzamide is obtained (yield 61percent-M.P.=126° to 127° C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With chloroformic acid ethyl ester; triethylamine; In acetone; at 0 - 30℃; | To a stirring mixture of 4-amino-2-methoxy-5 -ethyl sulphonyl benzoic acid (IV) and acetone (5.0 L) at 0-5°C, triethyl amine (0.405 Kg) was added and stirred followed by addition of ethyl chloroformate (0.368 Kg). N-ethyl-2-amino methyl pyrrolidine (0.627 Kg) was added to the reaction mass at 5-10°C. Temperature of reaction mass was raised to 25-30°C and stirred for 120 min. To the same reaction mass triethyl amine (0.405 Kg) and ethyl chloroformate (0.368 Kg) was added with maintaining the temperature. Reaction mass was stirred for 120 min. After completion of reaction, water (4.0 L) was added. Reaction mass was filtered and washed with water (2.0 L). Filtrate was collected and water was added (9.0 L). pH of the reaction mass was adjusted to 10.8-1 1.2 by using 20percent NaOH solution. Reaction mass was stirred for 240-300 min, filtered and washed with water. Solid was dried under vacuumYield : 70percentPurity: 98percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.5% | In glycerol; at 110 - 120℃; for 4.0h; | 25.9 g of <strong>[33045-53-3]ethyl 2-methoxy-5-sulfamoylbenzoate</strong>,1-ethyl-2-aminomethyltetrahydropyrrolidine 15g and glycerol 20g were added to the reaction flask,The reaction was carried out at 110-120 ° C for 4 hours, the reaction was completed, and it was cooled to 80 ° C.Add 40g of ethanol and stir for 10 minutes.Cool to 5 ° C and stir for 1 hour, filter,It was washed with ethanol and dried at 65 °C. The yield was 88.5percent and the purity was 99.5percent. |
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