Structure of 1355249-29-4
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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. : | 1355249-29-4 |
Formula : | C14H15IN2O3 |
M.W : | 386.19 |
SMILES Code : | O=C(C1=NN(CC2=CC=C(OC)C=C2)C=C1I)OCC |
MDL No. : | MFCD30180245 |
InChI Key : | YNEVUNLNNQEWHG-UHFFFAOYSA-N |
Pubchem ID : | 66668807 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 11 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 83.27 |
TPSA ? Topological Polar Surface Area: Calculated from |
53.35 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.0 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.72 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.35 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.07 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.84 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.14 |
Solubility | 0.0283 mg/ml ; 0.0000732 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.78 |
Solubility | 0.0634 mg/ml ; 0.000164 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.82 |
Solubility | 0.00579 mg/ml ; 0.000015 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
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) |
Yes |
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 |
-6.53 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.6 |
* 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 |
---|---|---|
58% | With potassium carbonate In acetonitrile at 60℃; | Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60°C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58percent).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): δ 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+. |
58% | With potassium carbonate In acetonitrile at 60℃; | Example 15, Step C[00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60°C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58percent).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): δ 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With potassium carbonate In acetonitrile at 20 - 60℃; Inert atmosphere | To a solution of ethyl 4-iodo-1H-pyrazol-3-formate (4.2 g, 15.8 mmol, 1.0 eq.) and potassium carbonate (4.37 g, 31.6 mmol, 2.0 eq.) in acetonitrile (45 mL) was added p-methoxybenzyl chloride (3.09 g, 19.7 mmol, 1.25 eq.) under stirring at room temperature. The reaction liquid was protected with nitrogen gas and stirred overnight at 60°C. The reaction liquid was cooled to room temperature and insoluble substances were filtered. The filter cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and separated by column chromatography on silica gel column to give ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazol-5-formate (C1, 1.94 g, 32percent yield) and ethyl 4-iodo-1-(4-methoxybenzyl)-1H-pyrazol-3-formate (C2, 2.90 g, 47percent yield). C1: 1H NMR (400MHz, CDCl3) δ 7.61 (s, 1H), 7.21 (d, J = 8.4 Hz, 2H), 6.82 (d, J = 8.4 Hz, 2H), 5.70 (s, 2H), 4.37 (q, J = 7.2 Hz, 2H), 3.77 (s, 3H), 1.40 (t, J = 7.2Hz, 3H). m/z=409[M+Na]+. C2: 1H NMR (400MHz, CDCl3) δ 7.36 (s, 1H), 7.22 (d, J = 8.8 Hz, 2H), 6.90 (d, J = 8.4 Hz, 2H), 5.31 (s, 2H), 4.44 (q, J = 7.2 Hz, 2H), 3.81 (s, 3H), 1.43 (t, J = 7.2Hz, 3H). m/z=409[M+Na]+. |
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