Structure of 344779-07-3
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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. : | 344779-07-3 |
Formula : | C9H19N3O |
M.W : | 185.27 |
SMILES Code : | O=C1N(CCN(C)C)CCNCC1 |
MDL No. : | MFCD03160593 |
InChI Key : | NEYJQNBUBDIATQ-UHFFFAOYSA-N |
Pubchem ID : | 3362131 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.89 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 59.89 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.58 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.23 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.96 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.25 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.15 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
-0.04 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.19 |
Solubility | 121.0 mg/ml ; 0.652 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
0.7 |
Solubility | 924.0 mg/ml ; 4.99 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.47 |
Solubility | 6.34 mg/ml ; 0.0342 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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 |
-8.11 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 |
1.0 |
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) |
1.91 |
* 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 33 4-(2-Dimethylaminoethyl)-1-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]-[1,4]diazepan-5-one Prepared from <strong>[344779-07-3]4-(2-dimethylaminoethyl)-[1,4]diazepan-5-one</strong> as described for Example 1, step c (0.035 g, 34%). deltaH (360 MHz; CDCl3) 2.25 (6H, s), 2.46 (2H, dd, J=7 and 7), 2.98-3.02 (2H, m), 3.56 (2H, dd, J=7 and 7), 3.73-3.88 (6H, m), 7.19-7.31 (2H, m), 7.35-7.39 (1H, m), 7.64 (1H, ddd, J=7, 7 and 1), 7.92 (1H, ddd, J=7, 7 and 1), 7.96 (1H, dd, J=8 and 1), 8.10 (1H, ddd, J=7, 7 and 2), 8.72 (1H, d, J =8); m/z (ES+) 448 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.4 mg | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20.0℃; for 27.0h; | General procedure: To a vial containing a solution of urea acid, 8a, (369.7 mg, 1 mmol), EDCI (230.8 mg, 1.2 mmol) and HOBt (147.6 mg, 1.1 mmol) in 1:1 DCM:N,N-dimethylformamide (DMF; 10 mL) was added 1,1-dioxothiomorpholine (133.1 mg, 1 mmol). The vial was capped, and the solution was stirred at room temperature for 27 h. The reaction mixture was diluted with EtOAc and washed with water (x3) and brine (x1). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Purification by silica flash column using 97:3 DCM:MeOH gave 401.0 mg (82%) of 13a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3 mg | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20.0℃; for 27.0h; | General procedure: To a vial containing a solution of urea acid, 8a, (369.7 mg, 1 mmol), EDCI (230.8 mg, 1.2 mmol) and HOBt (147.6 mg, 1.1 mmol) in 1:1 DCM:N,N-dimethylformamide (DMF; 10 mL) was added 1,1-dioxothiomorpholine (133.1 mg, 1 mmol). The vial was capped, and the solution was stirred at room temperature for 27 h. The reaction mixture was diluted with EtOAc and washed with water (x3) and brine (x1). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Purification by silica flash column using 97:3 DCM:MeOH gave 401.0 mg (82%) of 13a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; | Step 1: To a mixture of NaH (0.576 g, 24 mmol) in DMF (6 mL) at 0 C was added a solution of benzyl 5-oxo-1,4-diazepane-1-carboxylate (2.0 g, 8.1 mmol) in DMF (7 mL) and the mixture was then stirred at r.t. After 1 hour, the mixture was cooled to 0 C and a solution of 2-chloro-N,N-dimethylethanamine HCl (2.3 g, 16 mmol) in DMF (7 mL) was added and the final reaction mixture was stirred at r.t. overnight. The reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4, filtered and solvent was removed under vacuum. Purification by flash column (silica gel) gave 1.0 g (38%) of alkylated product. Step 2: To a solution of the above product (4.0 g, 12.5 mmol) in MeOH (80 mL) was added Pd/C (400 mg, 10%) and the reaction mixture was stirred at r.t. under hydrogen. After completion of the reaction, the mixture was filtered through celite. Solvent was removed under vacuum to give 1.8 g (77%) of 4-(2-(dimethylamino)ethyl)-1,4-diazepan-5-one. |
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