Structure of BFMO
CAS No.: 69010-90-8
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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.
Synonyms: N,N'-Difurfuryloxamide; N1,N2-Bis(furan-2-ylmethyl)oxalamide
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| CAS No. : | 69010-90-8 |
| Formula : | C12H12N2O4 |
| M.W : | 248.23 |
| SMILES Code : | O=C(NCC1=CC=CO1)C(NCC2=CC=CO2)=O |
| Synonyms : |
N,N'-Difurfuryloxamide; N1,N2-Bis(furan-2-ylmethyl)oxalamide
|
| English Name : | N1,N2-Bis(furan-2-ylmethyl)oxalamide |
| MDL No. : | MFCD00090454 |
| InChI Key : | XRURWFXKCKASSN-UHFFFAOYSA-N |
| Pubchem ID : | 330826 |
| Num. heavy atoms | 18 |
| Num. arom. heavy atoms | 10 |
| Fraction Csp3 | 0.17 |
| Num. rotatable bonds | 7 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 2.0 |
| Molar Refractivity | 60.85 |
| TPSA ? Topological Polar Surface Area: Calculated from |
84.48 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.24 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.44 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.5 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.16 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.22 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.65 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-1.61 |
| Solubility | 6.16 mg/ml ; 0.0248 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.78 |
| Solubility | 4.1 mg/ml ; 0.0165 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.16 |
| Solubility | 0.0173 mg/ml ; 0.0000695 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 |
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 |
-7.5 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) |
2.17 |
* 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 |
|---|---|---|
| 93% | In acetonitrile at 40℃; for 3h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; Cooling with ice; | General procedure: 2-Phenoxyaniline (30 mmol) and triethylamine (31.5 mmol) were dissolved in 100 mL of tetrahydrofuran, and the concentration of 2-phenoxyaniline was 0.3 mol/L. The mixture was cooled in an ice-water bath, and stirred. Then oxalyl chloride (15.8 mmol) was added dropwise. The system turned to turbid and triethylamide hydrochloride was formed. The ice-water bath was then removed and the mixture was warmed to room temperature in the air, and continuously stirred for 2 hours until 2-phenoxyaniline was completely consumed (monitored by TLC). Then the stirring was stopped for post process. The stirring bar was removed by a magnetic bar, and tetrahydrofuran was removed by evaporation under reduced pressure. 50 mL of distilled water was added to the resultant residue. The solid on the flask wall was scraped off and immersed into distilled water, and stirred to form slurry. Et3N.HCl was completely dissolved in water while the oxalic diamide was left undissolved. Then the slurry was filtered under reduced pressure, and the solid on filter paper was washed with cold diethyl ether. The residue was removed and dried in an infrared oven, and then dried with an oil pump to afford a white solid (5.45 g, 86% yield). 1H NMR (400 MHz, CDCl3) δ 9.96 (s, 2H), 8.46 (dd, J=8.0, 1.7 Hz, 2H), 7.43-7.30 (m, 4H), 7.22-7.01 (m, 10H), 6.89 (dd, J=8.0, 1.5 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 157.36, 156.06, 146.73, 129.97, 127.97, 125.40, 124.18, 123.75, 120.49, 119.02, 117.60; HRMS (ESI) calcd. for C26H21N2O4 (M+H)+: 425.1496, Found: 425.1492 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 4percent NaOH / methanol / 1 h / Ambient temperature 2: methanesulfonic acid / acetonitrile / 0.33 h / Ambient temperature 3: 93 percent / acetonitrile / 3 h / 40 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: methanesulfonic acid / acetonitrile / 0.33 h / Ambient temperature 2: 93 percent / acetonitrile / 3 h / 40 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Sealed tube; | |
| 86% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; | |
| 85% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; |
| 84% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; | |
| 50% | With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; | General procedure A General procedure: This compound was prepared following a literature procedure1. Add Et3N (2.5 equiv) to a solution of amine (2.0 equiv) in THF (0.3 M). Add oxalyl chloride (1.0 equiv) dropwise to the mixture at 0 °C. The reaction mixture was allowed to stir at room temperature for 4 h and water was added to the resulting residue to dissolve Et3N·HCl salt. Then the slurry was washed with water ( x 3) and cold ether ( x 3) on filter paper. These solids were dried in vacuo to afford the corresponding oxalamide. |
| With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | ||
| 85% | With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | |
| 85 % | With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | |
| With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | With potassium <i>tert</i>-butylate; [Ru(PtBuNNHBn)H(CO)Cl] In toluene at 135℃; for 24h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98 %Spectr. | With potassium <i>tert</i>-butylate; hydrogen; [Ru(PtBuNNHBn)H(CO)Cl] In toluene at 135℃; for 24h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: tetrahydrofuran / 2 h / 70 °C / Inert atmosphere |

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