Structure of 79349-82-9
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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. : | 79349-82-9 |
Formula : | C9H10N2O3S |
M.W : | 226.25 |
SMILES Code : | O=C(C(N12)=C(C=C)CS[C@]2([H])[C@H](N)C1=O)O |
MDL No. : | MFCD07782149 |
InChI Key : | GQLGFBRMCCVQLU-SVGQVSJJSA-N |
Pubchem ID : | 7280824 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 59.28 |
TPSA ? Topological Polar Surface Area: Calculated from |
108.93 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-2.78 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.33 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.55 |
Log S (ESOL):? ESOL: Topological method implemented from |
0.64 |
Solubility | 989.0 mg/ml ; 4.37 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
1.05 |
Solubility | 2520.0 mg/ml ; 11.1 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.15 |
Solubility | 317.0 mg/ml ; 1.4 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 |
-9.65 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) |
4.08 |
* 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 |
---|---|---|
88.6% | Stage #1: With triethylamine In tetrahydrofuran at 20 - 23℃; for 5 h; Stage #2: With hydrogenchloride; methoxybenzene In tetrahydrofuran; dichloromethane at -25 - -20℃; for 1.5 h; |
In a dry reaction flask, add 22.6g 7-AVCA, 43g cefdinir side chain active ester and 150 ml tetrahydrofuran. Control temperature 20 °C-23 °C. Add dropwise 12g triethylamine. Stir the reaction for 5h. HPLC measured end point of the reaction. After the reaction is complete, add 200 ml dichloromethane, anisole 30 ml. Cool to -25 °C- -20 °C. Place the dry hydrogen chloride gas. After about 1.5h, HPLC measured end point of the reaction. After the reaction, through N2In the system away excess hydrogen chloride gas, the temperature of not more than 0 °C, dropwise 5percent of K2CO3, Control pH value is 5.5 - 6.0, layered, in the aqueous phase by adding 80mLCH2Cl2Extraction, layered, in the aqueous phase by adding 2g activated carbon to decolorize 1h, filtering, adding water 400 ml, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 25 °C -28 °C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 35g, yield 88.6percent, purity of 99.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.8% | Stage #1: With triethylamine In N,N-dimethyl acetamide at 15 - 20℃; for 4 h; Stage #2: With hydrogenchloride; methoxybenzene In dichloromethane; N,N-dimethyl acetamide at -15 - -10℃; for 2 h; |
In a dry reaction flask, add 30g 7-AVCA, 85g cefdinir side chain active ester and 100 ml dimethylacetamide. Control temperature at 15 °C -20 °C. Add dropwise 30g triethylamine. Stir the reaction for 4h. The reaction completely becomes clear. After the reaction is complete, add 250 ml dichloromethane. Lower the temperature to -15 °C - -10 °C. Add 50 ml anisole. Place dry hydrogen chloride gas. After about 2h, HPLC measured end point of the reaction, the reaction after the end of the, through N2Away excess hydrogen chloride gas in the system. Then add 100 ml H2O, dropping 10percent of Na2CO3Solution, adjusting the pH value of 5.5 - 6.0, the temperature does not exceed 5 °C, layered. The aqueous phase is then added to 100 ml CH2Cl2Extraction, layered, add aqueous 3g decolorized with active carbon, the decolorization 1h after filtering, adding 500 ml water, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 20 °C -25 °C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 45g, yield 85.8percent, the purity is ≥ 99percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.6% | In a dry reaction flask, add 22.6g 7-AVCA, 43g cefdinir side chain active ester and 150 ml tetrahydrofuran. Control temperature 20 C-23 C. Add dropwise 12g triethylamine. Stir the reaction for 5h. HPLC measured end point of the reaction. After the reaction is complete, add 200 ml dichloromethane, anisole 30 ml. Cool to -25 C- -20 C. Place the dry hydrogen chloride gas. After about 1.5h, HPLC measured end point of the reaction. After the reaction, through N2In the system away excess hydrogen chloride gas, the temperature of not more than 0 C, dropwise 5% of K2CO3, Control pH value is 5.5 - 6.0, layered, in the aqueous phase by adding 80mLCH2Cl2Extraction, layered, in the aqueous phase by adding 2g activated carbon to decolorize 1h, filtering, adding water 400 ml, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 25 C -28 C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 35g, yield 88.6%, purity of 99.2%. | |
10.0 grams (44.2 mmol) of 7-amino-3-vinyl-3-cephem-4-carboxylic acid and 18.0 grams ( 44.7mmol) of (Z) - (2-amionthiazol-4-yl) -2-acetoxyiminoacetic acid 2- benzothiazolyl thioester were suspended in 100ml tetrahydrofuran and 40 ml DM water at room temperature and 4.7 grams (46.5mmol) of triethylamine was added. Then, the reaction mixture was stirred for 4-6 hrs at ambient temperature and 70 ml dichloromethane was added to reaction mixture and stirred for 10-30 minutes. Layers were separated and the aqueous layer treated with carbon, filtered, adjusted to pH 8.0- 8.2 with potassium carbonate solution, and the mixture stirred for 30-45 minutes at room temperature. The pH of the solution adjusted to 2-2.5 with sulfuric acid. The product obtained was filtered off, washed with water and dried to obtain 7-(Z)-[2-(2- amino-thiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid in a purity of 95%. | ||
Example 1; Step-I:T-Amino-S-vinyl-S-cephem^-carboxylic acid (40 gm) and 2-mercapto-1 ,3- benzothiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-(acetyloxyimino)-acetate (80 gm) are added to tetrahydrofuran (400 ml), stirred for 10 minutes, water (200 ml) is added at 250C and then the contents are cooled to 15 - 200C. Triethylamine (20 gm) is added and stirred for 3 - 4 hours at 15 - 200C. To the reaction mass methylenedichloride (400 ml) is added at 15 - 200C, stirred for 15 minutes and separated the organic layer. Aqueous layer is treated with activated carbon (4 gm) for 30 minutes while degassing. Filtered over hyflo bed and adjusted the pH of the aqueous layer to 8.1 - 8.5 with K2CO3 solution. Ammonium chloride (26.5 gm) is added and stirred at 20 - 250C for 30 minutes while maintaining the pH at 8.0 - 8.2. The temperature is raised to 35 - 400C, pH is adjusted to 2.4 - 2.5 with 50% sulfuric acid and stirred for 2 hours at the same temperature. Filtered EPO <DP n="7"/>the solid, washed with water (400 ml) and dried under vacuum at 40 - 45 C to give 60 gm of crude cefdinir (HPLC purity: 98.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.8% | In a dry reaction flask, add 30g 7-AVCA, 85g cefdinir side chain active ester and 100 ml dimethylacetamide. Control temperature at 15 C -20 C. Add dropwise 30g triethylamine. Stir the reaction for 4h. The reaction completely becomes clear. After the reaction is complete, add 250 ml dichloromethane. Lower the temperature to -15 C - -10 C. Add 50 ml anisole. Place dry hydrogen chloride gas. After about 2h, HPLC measured end point of the reaction, the reaction after the end of the, through N2Away excess hydrogen chloride gas in the system. Then add 100 ml H2O, dropping 10% of Na2CO3Solution, adjusting the pH value of 5.5 - 6.0, the temperature does not exceed 5 C, layered. The aqueous phase is then added to 100 ml CH2Cl2Extraction, layered, add aqueous 3g decolorized with active carbon, the decolorization 1h after filtering, adding 500 ml water, for 2 mol/L hydrochloric acid to adjust the pH value to 2.2 - 2.4, temperature control 20 C -25 C, nourishing crystal 2h after filtering, washing, alcohol washing, drying, to obtain cefdinir 45g, yield 85.8%, the purity is ? 99%. |
Tags: 79349-82-9 synthesis path| 79349-82-9 SDS| 79349-82-9 COA| 79349-82-9 purity| 79349-82-9 application| 79349-82-9 NMR| 79349-82-9 COA| 79349-82-9 structure
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
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 |
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