Structure of 712353-75-8
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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. : | 712353-75-8 |
Formula : | C13H15NO3 |
M.W : | 233.26 |
SMILES Code : | O=C(C1)N(CC2=CC=C(OC)C=C2)CCC1=O |
MDL No. : | MFCD17011792 |
InChI Key : | RWBJCFIEUAGKDV-UHFFFAOYSA-N |
Pubchem ID : | 46835622 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 67.03 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.61 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.85 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.78 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.24 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.36 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.88 |
Solubility | 3.08 mg/ml ; 0.0132 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.4 |
Solubility | 9.25 mg/ml ; 0.0397 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.44 |
Solubility | 0.0849 mg/ml ; 0.000364 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 |
-7.13 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) |
1.37 |
* 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 |
---|---|---|
49% | A suspension of methyl 3-amino, 5-phenylthiophene 2- carboxylate (459mg, 1.96mmol) and 1- (4-Methoxy-benzyl)- piperidine-2,4-dione (457mg, 1. 96MMOL) at 21, under N2, was treated with dibutyltin dichloride (29mg, 0.098mmol, 5mol%) followed after 5min with phenylsilane (266DOL, 233mg, 2.15mmol, L. leq). The HETEROGENOUS mixture was stirred for 18h at 21 when a clear solution resulted. The reaction was left a further 5H, then evaporated to a thick oil (1.27g). The crude material was purified over silica using (Hexanes : CH2CL2 : EtOAc = 1: 1 : 1) as eluent to deliver 3- [1- (4-METHOXY-BENZYL)-2-OXO-PIPERIDIN-4-YLAMINO]-5- (1- methyl-hexa-1, 3,5-trienyl)-thiophene-2-carboxylic acid methyl ester as a yellow foam (432mg, 49%) (300MHz, CDCl3) 1.8-1.9(m, 1H), 2.25-2. 44 (m, 1H), 2.95 (dd, J = 1. 5Hz, J = 3. 9OHZ, 1H), 3.98 (dd, J = 1. 5Hz, J = 3. 9OHZ, 1H), 3.22-3. 40 (m, 4H), 3.80 (s, 3H), 3.33 (s, 3H), 3.85- 3.93 (m, 1H), 4.08 (m, 2H), 6.81 (s, 1H), 6.85-6. 9 (m, 2H), 7.20-7. 24 (m, 2H), 7. 36-7. 42 (m, 3H), 7.59-7. 61 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | A mixture of an hydrous K2CO3 (3.2g, 23.2mmol, 5eq) and 18-crown-6 (azetroped several times with toluene) (122mg, 0. 464MMOL, 10MOL%) in dry toluene (4ML), under nitrogen, was heated to reflux and then treated, dropwise, over 40min, with a solution of N- (4-METHOXY- BENZYL)-N- (2-METHOXYCARBONYL-ETHYL)-MALONAMIC acid methyl ester. After 7h at reflux the reaction was diluted with water (4ML) and toluene (4ml), then cooled to 0 and carefully acudified to pH 1.7 with 0. 1N HC1. The mixture was then extracted several times with CH2C12 (3X80ML) and the combined organics dried and evaporated to a brown oil (1.33g). The brown oil was treated with 10% aqueous oxalic acid and heated to reflux for 6.5h. The mixture was then extracted repratedly with CH 2CL2 and the combined organics dried and evaporated to a dirty yellow oil (1.03g). The crude material was purified on silica gel using (CH2CL2 : MEOH 30: 1) as eluent to give 1- (4-METHOXY-BENZYL)- piperidine-2,4-dione as a pale brown solid (750mg, 69%) ; (300MHZ, CDC1 3) 2. 52 (T, J = 5.7HZ, 2H), 3.41 (s, 2H), 3.47 (t, J = 5.7Hz, 2H), 3.80 (s, 3H), 4.62 (s, 2H), 6.16-6. 88 (m, 2H), 7.20 (m, 2H). |
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