Structure of 19690-13-2
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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. : | 19690-13-2 |
Formula : | C8H12N2 |
M.W : | 136.19 |
SMILES Code : | CNCCC1=CC=CN=C1 |
MDL No. : | MFCD02089408 |
InChI Key : | WKRUEUNOCVALAM-UHFFFAOYSA-N |
Pubchem ID : | 5152594 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.62 |
TPSA ? Topological Polar Surface Area: Calculated from |
24.92 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.85 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.17 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.84 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.66 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.01 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.04 |
Solubility | 12.5 mg/ml ; 0.0917 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.25 |
Solubility | 76.4 mg/ml ; 0.561 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.24 |
Solubility | 0.078 mg/ml ; 0.000573 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 |
-7.01 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) |
1.3 |
* 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 |
---|---|---|
With hydrogen;palladium 10% on activated carbon; In methanol; at 50℃; | b) Title Compound; To a solution of benzyl-methyl-(2-pyridine-3-yl-ethyl-)amine (4.3 g) in methanol was added 10% palladium-carbon, and was stirred at 50 C. under hydrogen atmosphere for 1 hour. After filtrating with Celite, the filtrate was concentrated, and the title compound (2.39 g) was obtained as a colorless oily matter. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In mdf; at 20℃; for 18.0h; | A solution of Intermediate 13 (0.025g) in DMF (1ML) was treated with TEA (0. 025ML), a solution of TBTU (0.02mg) in DMF (0. 5ML) and finally with a SOLUTIONA3F N-METHYL-2- (3- pyridinyl) ethanamine (0.0102g) in DMF (0. 5ml). The mixture was stirred at ambient for 18h and then evaporated to dryness. The mixture was taken up in DMSO (0. 5ml), filtered and the desired product purified from the filtrate by means of mass-directed high performance liquid chromatography to give the title compound (0.0126g) as a white solid. Mass spectrum: Found: MH+ 563 H. p. l. c. Rt 2.64min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 47 1-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dion-3-yl)-3-[N-methyl-N-(2-(pyridyl-3)-ethyl)-amino]propane The title compound is prepared analogously to Example 31 by reacting 3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dion-3-yl)-propionaldehyde with <strong>[19690-13-2]3-(2-methylamino-ethyl)-pyridine</strong>, but with hydrogenation being carried out at ambient temperature. Melting point: 78-80 Celsius |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
N-(Cyclopropylmethyl)-2-(methyl(2-(pyridin-3-yl)ethyl)amino)-6-morpholinopyrimidine-4-carboxamide (Example 80) The title compound was prepared according to the general procedure E using 2-chloropyrimidine I-35 (30 mg, 0.10 mmol, 1 eq), <strong>[19690-13-2]N-methyl-2-(pyridin-3-yl)ethan-1-amine</strong> (21 muL, 0.15 mmol, 1.5 eq) and DiPEA (70 muL, 0.40 mmol, 4 eq). Total heating time: 17 h at 120 C. Column chromatography (2% -> 6% MeOH/DCM) afforded the product (11 mg, 29 mumol, 29%). TLC: Rf = 0.15 (4% MeOH/DCM). 1H NMR (400 MHz, CDCl3) delta 8.65 - 8.28 (m, 2H), 7.95 (br s, 1H), 7.51 (d, J = 7.9 Hz, 1H), 7.21 (dd, J = 7.9, 4.8 Hz, 1H), 6.72 (s, 1H), 3.89 - 3.69 (m, 6H), 3.69 - 3.53 (m, 4H), 3.29 (t, J = 6.4 Hz, 2H), 3.11 (s, 3H), 2.92 (t, J = 7.4 Hz, 2H), 1.12 - 0.99 (m, 1H), 0.66 - 0.45 (m, 2H), 0.36 - 0.19 (m, 2H). 13C NMR (101 MHz, CDCl3) delta 164.57, 163.95, 160.86, 156.77, 150.27, 147.86, 136.33, 135.30, 123.50, 90.36, 66.74, 51.19, 44.49, 44.15, 35.84, 31.23, 10.91, 3.51. HRMS [C21H28N6O2 + H]+ : 397.2347 calculated, 397.2345 (found (Delta = -0.38 ppm). |
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