Structure of 944805-17-8
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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. : | 944805-17-8 |
Formula : | C9H11BrN2O3S |
M.W : | 307.16 |
SMILES Code : | O=C(OC(C)(C)C)NC1=NC(Br)=C(C=O)S1 |
MDL No. : | MFCD18836517 |
InChI Key : | JYXJVZYNONJDLM-UHFFFAOYSA-N |
Pubchem ID : | 45117881 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 16 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.44 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 65.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
96.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.71 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.23 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.33 |
Solubility | 0.144 mg/ml ; 0.00047 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.35 |
Solubility | 0.0138 mg/ml ; 0.0000448 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.03 |
Solubility | 0.285 mg/ml ; 0.000929 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) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
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 |
-6.28 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 |
0.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.08 |
* 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 |
---|---|---|
70% | To a solution of diisopropylamine (3.3 mL, 23 mmol) in THF (20. mL) at 0 C was added n-butyllithium (14.8 mL, 1.6 M in hexanes) slowly. The reaction was stirred for 20 minutes and then tert- butyl (5- bromothiazol-2-yl)carbamate (2.00 g, 7.16 mmol) was added slowly as a solution in THF (20. mL). The mixture was stirred for 30 minutes at 0 C and then DMF (1.8 mL, 23 mmol) was added. The solution was stirred for 2h at rt. EA and water were added, the layers were separated, and the organics were washed with brine. The organics were dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography using ethyl acetate in heptane as eluent to yield the title compound (1.53 g,70% yield). LCMS (ESI): [M+H] 308.9 for 81Br. 1HNMR: (400 MHz, Methanol- 4) d 9.83 (s, 1H), 1.56 (s, 9H). | |
64% | Example 18, Step F[00180] To (i-Pr)2NH (59.7 g, 0.591 mol) in THF (250 mL) at 0C was added n-BuLi (236 mL, 2.5 M, 0.591 mol) was added slowly. The reaction mixture was stirred for 20 mins after which a THF solution of compound 15_2 (50 g, 0.179 mol) was slowly added to the reaction mixture with continued stirring. The mixture was stirred for 30 mins at 0C and then DMF (43.1 g, 0.591 mol) added. The mixture was stirred for 12 hrs at r.t. and diluted with EtOAc and water. The organic layer was separated, washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by silica chromatography to give compound 18_1 (35 g, 64%) as a white solid. [00181] This compound was characterized by proton NMR (1HNMR) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 9.73(s, 1 H); 1.47(s, 9H). | |
64% | Example 18, Step F[00180] To (i-Pr)2NH (59.7 g, 0.591 mol) in THF (250 mL) at 0C was added n-BuLi (236 mL, 2.5 M, 0.591 mol) was added slowly. The reaction mixture was stirred for 20 mins after which a THF solution of compound 15_2 (50 g, 0.179 mol) was slowly added to the reaction mixture with continued stirring. The mixture was stirred for 30 mins at 0C and then DMF (43.1 g, 0.591 mol) added. The mixture was stirred for 12 hrs at r.t. and diluted with EtOAc and water. The organic layer was separated, washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by silica chromatography to give compound 18_1 (35 g, 64%) as a white solid. [00181] This compound was characterized by proton NMR (1HNMR) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 9.73(s, 1 H); 1.47(s, 9H). |
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