Structure of 305790-48-1
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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. : | 305790-48-1 |
Formula : | C8H7BrN2O |
M.W : | 227.06 |
SMILES Code : | O=C1N(C)C2=CC(Br)=CC=C2N1 |
MDL No. : | MFCD09759338 |
InChI Key : | WQXHBMNNVRGWHF-UHFFFAOYSA-N |
Pubchem ID : | 9815982 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 51.52 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.79 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.93 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.44 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.63 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.9 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.83 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.71 |
Solubility | 0.443 mg/ml ; 0.00195 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.84 |
Solubility | 3.29 mg/ml ; 0.0145 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.24 |
Solubility | 0.131 mg/ml ; 0.000575 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) |
Yes |
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 |
-6.66 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 |
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) |
1.62 |
* 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 |
---|---|---|
63% | at 80℃; Inert atmosphere | 5-Bromo-N1-methylbenzene-1,2-diamine (14 g, 69.3 mmol) was dissolved in THF (200 mL), CDI (13.4 g, 83.2 mmol) was added. The mixture was reflux about 2 hours under N2. When LCMS showed the staring material was consumed, the solvent was evaporated and the resulting crude was purified by column chromatography on silica gel (EA : PE = 1 : 2) to give the product 6-bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one (10 g, yield 63 percent). 1H NMR (400 MHz, DMSO -d ) δ 11.0 (s, 1H), 7.33 (s, 1H), 7.13 (t, J= 8.0 Hz, 1H), 6.92 (d, J= 8.0 Hz, 1H), 3.26 (s, 3H). LC-MS (ESI+): m/z 228.1 (M+H)+. |
63% | at 80℃; Inert atmosphere | 5-Bromo-Nl-methylbenzene-l,2-diamine (14 g, 69.3 mmol) was dissolved in THF (200 mL), CDI (13.4 g, 83.2 mmol) was added, the mixture was reflux about 2 hours under N2. The staring material was consumed, evaporated the solvent, the crude was purified with column (EA : PE = 1 : 2), 10 g of target compound was obtained (63 percent yield). NMR (400 MHz, DMSO -d6) δ 11.0 (s, 1H), 7.33 (s, 1H), 7.13(t, J= 8.0 Hz, 1H), 6.92(d, J= 8.0 Hz, 1H), 3.26(s, 3H); LC- MS (ESI+): m/z 228.1 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 20℃; for 18 h; | [00338] 6-Bromo-l-methyl-lH-benzo[d]imidazol-2(3H)-one: tert-Butyl 5- bromo-2-oxo-2,3-dihydrobenzo[d]imidazole-l-carboxylate (12 g, 38 mmol) (Puwen Zhang, et. al., Bioorganic Medicinal Chemistry Letters 1 1 (2001) 2747-2750 hereby incoporated by reference) and anhydrous disodium carbonate (3.2 niL, 77 mmol) were mixed in 200 mL THF. To this mixture was added dimethyl sulfate (15 mL, 153 mmol). The mixture was stirred at room temperature for 18 hours. The solvent was evaporated. The residue was dissolved in EtOAc and washed with brine and dried over sodium <n="159"/>sulfate. The solvent was evaporated. The residue was taken up in MeOH (50 mL) and allowed to stand 18 hours. The solvent was evaporated, and the residue was triturated from MeOH (25 mL) to provide the product as a white solid (8.7 g, 100 percent). LCMS (API- ES) m/z: 227, 229 (M+H*). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | Stage #1: for 18 h; Reflux Stage #2: With hydrogenchloride In water for 12 h; |
To a solution of2-amino-4-bromobenzenethiol (500 mg,2.50 mmol)in acetic acid (25mL)was added triphosgene (490 mg,1.70 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature,the solution was partially concentrated under reducedpressure,water was added,and the resulting precipitate was removed via filtration,and washedwith aqueous NaOH (1M). The filtrate was acidified with aqueous HCl (2 N)to pH 2,and placed in a refrigerator for 12 h. The resulting precipitate was filtered,washed with water,anddried under reduced pressure to give the title compound (133 mg,24percent)as a while powder thatrequired no further purification. 1H NMR (400 MHz,DMSO-d6)8 10.97 (s,1H),7.33 (d,J = 1.9Hz,1H),7.13 (dd,J = 8.2,1.9 Hz,1H),6.91 (d,J = 8.2 Hz,1H),3.26 (s,3H) |
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