Structure of 38362-15-1
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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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Batch number can be found on the product's label following the word 'Batch'.
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.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 38362-15-1 |
Formula : | C2HClN2S |
M.W : | 120.56 |
SMILES Code : | ClC1=NC=NS1 |
MDL No. : | MFCD09743974 |
InChI Key : | RZKVGQCJNANFDR-UHFFFAOYSA-N |
Pubchem ID : | 548032 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 6 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 24.92 |
TPSA ? Topological Polar Surface Area: Calculated from |
54.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.46 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.72 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.19 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.65 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.97 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.34 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.29 |
Solubility | 0.622 mg/ml ; 0.00516 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.47 |
Solubility | 0.408 mg/ml ; 0.00338 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.49 |
Solubility | 3.91 mg/ml ; 0.0324 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 |
-5.81 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 |
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) |
2.48 |
* 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 7 (R,R,)-2-(tert-Butyloxycarbonyl-5-(1,2,4-thiadiazol-5-yl)-2,5-diazabicyclo[2.2.1]heptane The title compound is prepared by the procedure of Example 5 using the product from Example 1, 5-chloro-1,2,4-thiadiazole prepared by the procedure of J. Goerdeler, Chim. Ber., 1957, 90, 182, and potassium carbonate to give 0.94 g of the desired product: [alpha26°D =+175° (c=1.3percent), methyl alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 8 (S,S)-2-(tert-Butyloxycarbonyl)-5-(1,2,4-thiadiazol-5-yl)-2,5-diazabicyclo[2.2.1]heptane The title compound is prepared by the procedure of Example 5 using the product from Example 2, 5-chloro-1,2,4-thiadiazole prepared as above, and potassium carbonate to give 2.4 g of the desired product: [alpha26°D =-190° (c=1.0percent), methyl alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Parallel preparation of Examples 145-148: To a set of vials individually containing requisite aryl chloride or bromide (0.063 mmol) and Cs2C03 (51 mg, 0.16 mmol) was added a solution of the piperazine from Scheme C (25 mg, 0.052 mmol) in THF (1 mL). The vials were capped and transferred to a glove box under an atmosphere of nitrogen. To each vial was added chloro(2-dicyclohexylphosphino-2',6'-di-i-propoxy-l,l '- biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (Strem) (2.1 mg, 0.0026 mmol). The vials were capped and heated at 80°C overnight. The vials were cooled to RT and removed from the glove box. To each vial was added water. The mixtures were extracted with CH2C12 and the organic layers were transferred into a new set of vials. The organic layers were dried in vacuo. To each vial was then added THF:MeOH (1 :3, 1 mL) followed by HC1 (4 N in dioxane, 0.20 mL, 0.80 mmol). The vials were capped and the solutions were heated to 70°C for 0.5 h. The solutions were allowed to cool to RT and the solvent was then removed in vacuo. Each crude product was redissolved in 1 mL of DMSO and filtered. The crude products were purified by mass triggered HPLC. Examples 145-146 were purified using the following conditions: [Waters Sunfire C18 column, 5muetaiota, 19x100 mm, gradient 10percent to 60percent MeCN (0.1percent formic acid) in water (0.1 percent formic acid) 50 mL/min, 8 min run time] Examples 147-148 were purified using the following conditions: [Waters XBridge CI 8 column, 5muiotaeta, 19x100 mm, gradient ranges from 10percent initial to 70-76percent MeCN (0.1percent NH4OH) in water (0.1percent NH4OH) 50 mL/min, 8 min run time]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20℃; | A solution of dry MeCN (226 mg, 11 mmol) in dry THF (25 ml) was added LiHIVIDS (5.5 mmol, 5.5 mL) at 0 °C, then the mixture was stirred at 0 °C for 30 mi 5-chloro-1,2,4- thiadiazole (691 mg, 5.5 mmol) in dry THF (5 mL) was added to the mixture at 0 °C, then stirred at rt overnight. The reaction mixture was quenched by H20 (1 mL), and extracted by EA (30 mL X 3), dried with Na2SO4, filtered and dried in vacuo to afford the crude product. Further purification by column chromatography (Si02, 100 g, 200-3 00 m, eluted by PE/EA = 5:1) gave the desired product (410 mg, 60percent) as yellow solid. MS [M+H] calcd for C4H3N35126.0, found 126.0. |
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