Structure of 21594-52-5
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 21594-52-5 |
Formula : | C6H3BrN2O2 |
M.W : | 215.00 |
SMILES Code : | BrC1=CN=C2C(=C1)OC(N2)=O |
MDL No. : | MFCD08689590 |
InChI Key : | VQPBRWIFFBIRRP-UHFFFAOYSA-N |
Pubchem ID : | 13614458 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.33 |
TPSA ? Topological Polar Surface Area: Calculated from |
58.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.39 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.09 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.28 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.82 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.37 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.47 |
Solubility | 0.737 mg/ml ; 0.00343 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.92 |
Solubility | 2.59 mg/ml ; 0.0121 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.31 |
Solubility | 0.106 mg/ml ; 0.000492 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 |
-6.84 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) |
2.41 |
* 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 |
---|---|---|
98% | With sodium hydroxide; water;Heating / reflux; | 2: 6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ~7. A lot of CO2 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98percent yield). |
98% | 6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ~7. A lot of C02 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98percent yield). | |
80 - 93% | To a solution of 6-bromo-3H-oxazolo[4,5-.pound.]pyridin-2-one (28.0 g, 130 mmol) in MeOH (280 mL) was added a solution of NaOH (28.1 g, 703 mmol) in water (280 mL). The mixture was heated to reflux overnight. The organic solvent was removed in vacuo and the aqueous mixture was adjusted to peta 5-6 with 12 M HCl. The resulting precipitate was isolated by filtration, washed with Et2psi and dried under vacuum at 50 °C overnight to give the title compound (19.6 g, 80percent) as a gray solid: 1H NMR (500 MHz, DMSO-cfc) delta 10.1 (s, IH), 7.46 (d, J= 1.5 Hz, IH), 6.88 (s, IH), 5.70 (s, 2H); ESI MS m/z 190 (M + H)+.; To a suspension of 6-bromo-3H-oxazolo[4,5-]pyridin-2-one (20.0 g, 93.0 mmol) in methanol (200 mL) was added NaOH (20.0 g, 500 mmol) in H2O (200 mL) and the mixture was heated to reflux overnight. After cooling, methanol was removed in vacuo. The aqueous residue was acidified with 3N HCl to pH 5-6. The resulting precipitate was collected by filtration, and dried overnight under vacuum at 45 0C to give the title compound as a tan solid (16.4 g, 93percent): 1H NMR (300 MHz, DMSO-^) delta 10.03 (s, IH), 7.47 (d, J= 2.0 Hz, IH), 6.93 (d, J= 2.0 Hz, IH), 5.72 (s, 2H); ESI MS m/e 188 (M + H)+. |
80% | [00104] As shown in step 4-iii of Scheme 20, Compound 1012 (34 g, 158.1 mmol) was diluted with 10percent NaOEta(aq) (500 mL), and the resulting mixture was stirred at 100 0C for 6 h. The reaction was cooled to 5 0C, and 6 N HCl was added until a precipitate formed (ca. pH 10). The solid was collected in a fritted funnel, washed with water (200 mL), and dried under vacuum to afford 2-amino-5-bromo-3-hydroxypyridine (Compound 1013, 24.0 g, 80percent yield) as a tan solid: ESMS (M+H) 189, 191; 1H NMR (DMSO-d6) delta 7.5 (s, IH), 6.9 (s, IH), 5.7 (br, 2H). | |
80% | As shown in step 4-iii of Scheme 20, Compound 1012 (34 g, 158.1 mmol) was diluted with 10percent NaOEta(aq) (500 mL), and the resulting mixture was stirred at 100 0C for 6 h. The reaction was cooled to 5 0C, and 6 N HCl was added until a precipitate formed (ca. pH 10). The solid was collected in a fritted funnel, washed with water (200 mL), and dried under vacuum to afford 2-amino-5-bromo-3-hydroxypyridine (Compound 1013, 24.0 g, 80percent yield) as a tan solid: ESMS (M+H) 189, 191; 1H NMR (DMSO-d6) delta 7.5 (s, IH), 6.9 (s, IH), 5.7 (br, 2H). | |
With water; sodium hydroxide; for 4h;Reflux; | 6-bromo[1 ,3]oxazolo[4,5-o]pyridin-2(3H)-one (I-52) (69 g, 0.3 mol) was added to 10percent aqueous sodium hydroxide (600 ml_) and the mixture was refluxed for 4 h. TLC (EtOAc/hexane= 1 :2) indicated the reaction was complete. The mixture was cooled to room temperature and acidified to pH~7 by dropwise addition of 10percent HCI (300 mL). The precipitate formed was filtered, washed with water (100 mL) and dried undervacuum to afford 2-amino-5-bromopyridin-3-ol (I-53) (58 g, 73percent) as a yellow solid, which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In dichloromethane; at 0 - 40℃; for 3h;Inert atmosphere; | Compound WXO7O-4 (300.00 mg, 1.59 mmol) was dissolved in dichloromethane (20.00 mE) and pyridine (10. 00 mE), followed by the addition oftriphosgene (471.83 mg,1.59 mmol) at 0 C. The reaction mixture was heated to 40 C. and stirred for 3 hours under nitrogen atmosphere. After the reaction, the mixture was diluted with water (20 mE). The separated aqueous phase was extracted with dichloromethane (20 mEx3). The organic phases were combined, washed with saturated brine (20 mE) and dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent. The obtained residue was isolated by silica gel colunm chromatography (eluent: petroleum ether/ethyl acetate=1 0/ 1-1/1, volume ratio) to obtain the target product WXO7O-5. ?H NMR (400 MHz, MeOD) oe: 8.14 (d, J=2.0 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H). |
A228930 [1207175-73-2]
tert-Butyl (5-bromo-3-hydroxypyridin-2-yl)carbamate
Similarity: 0.88
A195862 [34950-82-8]
7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
Similarity: 0.75
A196227 [122450-96-8]
7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.74
A270681 [748812-61-5]
tert-Butyl (5-bromo-3-methylpyridin-2-yl)carbamate
Similarity: 0.72
A113985 [207799-10-8]
tert-Butyl (4-bromopyridin-2-yl)carbamate
Similarity: 0.71
A228930 [1207175-73-2]
tert-Butyl (5-bromo-3-hydroxypyridin-2-yl)carbamate
Similarity: 0.88
A252393 [35570-68-4]
6-Chlorooxazolo[4,5-b]pyridin-2(3H)-one
Similarity: 0.80
A217578 [902835-93-2]
tert-Butyl (3-hydroxypyridin-2-yl)carbamate
Similarity: 0.76
A196227 [122450-96-8]
7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.74
A270681 [748812-61-5]
tert-Butyl (5-bromo-3-methylpyridin-2-yl)carbamate
Similarity: 0.72
A252393 [35570-68-4]
6-Chlorooxazolo[4,5-b]pyridin-2(3H)-one
Similarity: 0.80
A195862 [34950-82-8]
7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
Similarity: 0.75
A196227 [122450-96-8]
7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.74
A149223 [53052-06-5]
Oxazolo[4,5-b]pyridine-2(3H)-thione
Similarity: 0.68
A105591 [894852-01-8]
7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Similarity: 0.66