Structure of 22387-37-7
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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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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 22387-37-7 |
Formula : | C6H7N5 |
M.W : | 149.15 |
SMILES Code : | NC1=C2NC(C)=NC2=NC=N1 |
MDL No. : | MFCD19237006 |
InChI Key : | ORUIZIXJCCIGAI-UHFFFAOYSA-N |
Pubchem ID : | 95187 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 41.05 |
TPSA ? Topological Polar Surface Area: Calculated from |
80.48 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.17 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-0.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.81 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.37 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.03 |
Solubility | 1.39 mg/ml ; 0.0093 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.33 |
Solubility | 0.696 mg/ml ; 0.00467 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.17 |
Solubility | 0.997 mg/ml ; 0.00668 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 |
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 |
-6.46 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) |
1.82 |
* 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 |
---|---|---|
11% | at 240.0℃; for 6.0h; | Example 109; Synthesis of 2- (6-Arnino-8-methyl-vurin-9-yl)-5-hydroxMeLhyl-tetrahvdro- furan-3, 4-diol; Step 1; Synthesis of 8-Methyl-9H-purin-6-ylamine; 4,5, 6-Triaminopyrimidine sulfate (3. 0g, 13.4mmol) and acetamide (l. Og, 16. 9mmol) were added to a 25mL autoclave bomb and heated to 240C for 6 hours. The crude product was then boiled in H20 for 1 hour and filtered through a small pad of Celite. The flow through was concentrated and purified by HPLC 0-10% Buffer B over 30min at a flow rate of lOmLs/min. Buffer A-0. 1% triethylammonium acetate in water, Buffer B-0. 1 % triethylammonium acetate in CH3CN. Pooled the appropriate fractions and concentrated in vacuo to give 225mg (11 %) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane; for 24.0h;Heating / reflux; | Step 2; Synthesis of N, N-Dimethyl-N'- (8-methyl-9H-purin-6-yl)-formamidine; To a suspension of the product in Step 1 above (225mg, 1. 5 lmmol) in MeOH (14mL) and methylene chloride (7mL) was added N'N'-dimethylformamide dimethyl acetal (0. 8mL, 4. 52mmol) and the mixture heated to reflux for 24 hours. The resuling yellow solution was concentrated in vacuo to a yellow oil. This oil was co- evaporated with methylene chloride (2 x 15mL) and held under high vacuum for 2hours. The crude product was used directly in Step 3, without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tin(IV) chloride; In acetonitrile; at 20.0℃; | dry acetonitrile (50 mL) solution of 7 (1.10g,2.79mmol) was treated with 8-methyl adenine and stannic chloride (SnCl4,660L,5.58mmol), and stirred at room temperature overnight. The solution wasconcentrated under reduced pressure, and diluted with chloroform (100 mL), andtreated with cold saturated aqueous NaHCO3 solution (100 mL). Themixture was filtered through Celite and the precipitate was washed with hot chloroform.The combined filtrates were washed with water (100 mL) and brine (100 mL), and dried(Na2SO4), and evaporated under reduced pressure. Theresidue was purified by silica gel column chromatography [eluent: methanol (3%to 5%) / step gradient of methylene chloride] to give 20 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.2% | With caesium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 5.0h; | Example 16-Preparation of (1R,3R)-methyl 3-(6-amino-8-methyl-9H-purin-9-yl)cyclopentanecarboxylate (Compound 9o) <strong>[22387-37-7]8-Methyladenin</strong>e (compound 80o, 200 mg, 1.3409 mmoles) and compound 5 (387 mg, 1.743 mmoles) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and cesium carbonate (437 mg, 1.3409 mmoles) was added. The resulting mixture was stirred at 80 deg C. for 5 hours. After cooling to room temperature, the mixture was filtered and concentrated to dryness. Purification on basic alumina (1% methanol in dichloromethane) gave compound 9o (130 mg, 35.2% yield) as an off-white solid. 1HNMR (500 MHz, DMSO-d6) delta ppm: 8.1 (s, 1H), 7.0 (brs, 2H), 4.9 (m, 1H), 3.7-3.6 (s, 6H), 3.2 (m, 1H), 2.4-2.2 (m, 6H): Mass (m/z): 276.5 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | In N,N-dimethyl-formamide; at 85.0℃; | A mixture of <strong>[22387-37-7]8-methyl-9H-purin-6-ylamine</strong> (150 mg, 1.0 mmol) and l,3-dichloro-2- chloromethyl-benzene (214 mg, 1.1 mmol) in DMF (3 mL) was stirred at 85 C overnight. The mixture was cooled and filtered. The filtrate was purified by prep-HPLC (NH4HCO3 system) to give 3-(2,6-dichloro-benzyl)-8-methyl-3H-purin-6-ylamine (2 mg, yield: 5 %) as white solid. 1H NMR (400 MHz, DMSO- d): d = 7.82 (s, 1H), 7.70 (brs, 2H), 7.60-7.58 (m, 2H), 7.51-7.47 (m, 1H), 5.67 (s, 2H), 2.38 (s, 3H). MS: m/z 308.0 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 95.0℃;Inert atmosphere; | A flask charged with 8-bromo-9H-purin-6-ylamine (500 mg, 2.3 mmol), methylboronic (200 mg, 3.5mmol), Pd(dppf)Cl2 (84 mg, 0.115 mmol) and K2C03 (938 mg, 0.9 mmol) in dioxane/H20 (50 mL/l0 mL) was degassed and filled with N2. The mixture was stirred at 95 C overnight. Solvent was removed and the residue was purified with prep-TLC (DCM/MeOH = 10/1) to give 8-methyl-9H-purin-6-ylamine (150 mg, yield: 43 %) as yellow solid. MS: m/z 150.0 (M+H+). |
A205443 [6055-72-7]
7H-Purin-6-amine hydrochloride hydrate (2:2:1)
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7H-Purin-6-amine hydrochloride hydrate (2:2:1)
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