Structure of 214147-60-1
*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. : | 214147-60-1 |
Formula : | C12H13ClN2O2 |
M.W : | 252.70 |
SMILES Code : | O=C(N1C(Cl)=NC2=CC=CC=C12)OC(C)(C)C |
MDL No. : | MFCD21099394 |
Boiling Point : | No data available |
InChI Key : | NSCSJISDXDCCGL-UHFFFAOYSA-N |
Pubchem ID : | 23441223 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 66.95 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.71 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.47 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.16 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.91 |
Solubility | 0.0309 mg/ml ; 0.000122 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.29 |
Solubility | 0.0131 mg/ml ; 0.0000518 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.61 |
Solubility | 0.0626 mg/ml ; 0.000248 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-5.24 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) |
2.3 |
* 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 dmap; In acetonitrile; | Preparation 46 tert-Butyl 2-chloro-1H-1,3-benzimidazole-1-carboxylate 2-Chloro-1H-1,3-benzimidazole (1.07 g) was added to a solution of di-tert-butyldicarbonate (1.83 g) and 4-dimethylaminopyridine (86 mg) in acetonitrile (15 ml). The reaction mixture was stirred at room temperature for 30 minutes, after which time the solvent was removed under reduced pressure. The crude product was then purified by column chromatography on silica gel eluding with a solvent gradient of 100:0 changing to 90:10, by volume, hexane:ethyl acetate to afford tert-butyl 2-chloro-1H-1,3-benzimidazole-1-carboxylate (1.68 g) as a white solid. 1H-NMR (CDCl3) delta: 7.90 (1H, m), 7.35 (1H, m), 7.40 (2H, m), 1.80 (9H, s). MS: 253 (MH+). | |
With triethylamine; In isopropyl alcohol; at 20℃; for 19.0h;Product distribution / selectivity; | Example 1. 4- (2- ( (2, 6-Dimethylphenyl) oxy)-1H-benzimidazol-1-yl)-N- (4- (4- methyl-l-piperazinyl) phenyl)-2-pyrimidinamine; Step A: 2-Chloro-benzoimidazole-l-carboxylic acid tert-butyl ester; Di-tert-butyldicarbonate (12.270 g, 56.221 mmol) was added to a solution of 2- chlorobenzimidazole (8. 41 g, 55.119 mmol) and triethylamine (20 mL) in isopropanol (90 mL). The reaction mixture was stirred at room temperature for 19 h and then concentrated. The resulting material was purified via column chromatography on silica gel (eluting with dichloromethane) to afford 2-chloro- benzoimidazole-1-carboxylic acid tert-butyl ester as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In isopropyl alcohol; at 150℃; for 17.0h; | Step B: 2- (2-Methoxy-phenoxy)-lH-benzoimidazole; Cesium carbonate (3.965 g, 12.17 mmol) was added to a solution of 2-chloro- benzoimidazole-1-carboxylic acid tert-butyl ester (1.500 g, 5.936 mmol) and 2- methoxyphenol (5.90 g, 5.20 mL, 47.5 mmol) in isopropanol (25 mL). The mixture was heated at 150 C for 17 h and was then cooled to room temperature. The reaction mixture was partitioned between ethyl acetate and 2.0 N sodium hydroxide solution. The aqueous phase was separated and extracted with ethyl acetate and dichloromethane. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford an off-white solid. Trituration with ethyl acetate and filtering afforded 2- (2-methoxy-phenoxy)- 1H-benzoimidazole as a white solid. MS (MH+) 240. 8 ; Calculated 240.09 for Ct4Hi2N202. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In isopropyl alcohol; at 150℃; for 22.0h; | Step B: 2-(2, 6-Dimethyl-phenoxy)-lH-benzoimidazole; Cesium carbonate (2.643 g, 8. 112 mmol) was added to a solution of 2-chloro- benzoimidazole-l-carboxylic acid tert-butyl ester (1.000 g, 3.957 mmol) and 2,6- dimethylphenol (3. 867 g, 31.66 mmol) in isopropanol (10 mL). The mixture was heated at 150 C for 22 h and then cooled to room temperature. The reaction mixture was partitioned between ethyl acetate and 2.0 N sodium hydroxide solution. The aqueous phase was separated and extracted with ethyl acetate and dichloromethane. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford an orange-brown solid. Trituration with dichloromethane and filtering afforded 2- (2, 6-dimethyl- phenoxy)-lH-benzoimidazole as an off-white solid. MS (MH+) 239.2 ; Calculated 238.11 forCl5Hl4N2O. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
627 mg (99%) | EXAMPLE 30 4-(1H-BENZOIMIDAZOL-2-YL)-1,4-DIAZA-BICYCLO[3.2.2]NONANE Di-tert-butyl dicarbonate (600 mg, 2.75 mmol) was added to a solution of 2-chloroimidazole (381 mg, 2.50 mmol), and sodium hydroxide (120 mg, 3.0 mmol) in tetrahydrofuran (2.5 mL) and water (2.5 mL). After 3 h at RT an additional portion of di-tert-butyl dicarbonate (100 mg, 0.46 mmol) was added and the mixture was stirred at RT for 16 h. The mixture was extracted with ethyl acetate (3*) and the combined organic layers were dried (Na2SO4), filtered and concentrated to afford 627 mg (99%) of 2-chloro-benzoimidazole-1-carboxylic acid tert-butyl ester which was used without further purification: MS (Cl) m/z 253.1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
104 mg (34%) | With ammonium hydroxide; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In chloroform; toluene; | 2-Chloro-benzoimidazole-1-carboxylic acid tert-butyl ester (333 mg, 1.32 mmol), 1,4-diazabicyclo[3.2.2]nonane (57%, 195 mg, 0.88 mmol), tris(dibenzylideneacetone)dipalladium (28 mg, 0.031 mmol), racemic-2,2'-bis(diphenylphosphino)-1,1 '-binaphthyl (58 mg, 0.093 mmol), sodium tert-butoxide (208 mg, 2.17 mmol) and toluene (1.55 mL) were added to a flame dried round bottom flask purged with nitrogen. The mixture was placed in an oil bath at 80 C. for 18 h and then cooled to RT. The mixture was filtered through a pad of celite and washed with chloroform and methanol. The filtrate was concentrated and the residue was purified by chromatography (Biotage, 12M) eluding with 8% methanol in chloroform with 20 drops of NH4OH per liter of eluent to afford 104 mg (34%) of 2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-benzoimidazole-1-carboxylic acid tert-butyl ester: MS (Cl) m/z 343.1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 47 tert-Butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate The title compound was prepared by a similar method to Preparation 2 from tert-butyl 2-chloro-1H-i1,3-benzimidazole-1-carboxylate [see Preparation 46] and benzyl (2S)-2-piperidinecarboxylate [see J.A.C.S. (1 996), 118(7), 1629-1644]. The crude product was purified by column chromatography on silica gel eluding with a solvent gradient of 90:10 changing to 80:20, by volume, hexane:ethyl acetate, in 5% increments to afford tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate as an oil. 1H-NMR (CDCl3) delta: 7.65 (1H, d), 7.45 (1H, d), 7.40 (2H, s), 7.25 (5H, m), 5.20 (2H, s), 4.70 (1H, m), 4.65 (1H, m), 3.60 (1H, m), 2.20 (1H, m), 2.05 (1H, m), 1.80-1.50 (13H, m). MS: 436 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.2 mg. (37%) | With sodium hydroxide; trifluoroacetic acid; In dichloromethane; chloroform; water; | Example 8 5-(Benzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (150 mg, 0.413 mmol) and 1-t-butyloxycarbonyl-2-chlorobenzimidazole (104 mg, 0.413 mmol) were converted to the title compound by the procedure of Example 7 except that after chromatography there was a mixture of protected and de-protected products. Therefore, 80 mg of the mixture was dissolved in 20 mL of dichloromethane and 1 mL of trifluoroacetic acid was added. The mixture was stirred for 2 hours and then taken up in water. The reaction was partitioned between 3 mL of 1N aqueous sodium hydroxide and 3 mL of 3:1 chloroform:isopropanol to give 51.2 mg. (37%). MS(FD) m/e 331.8 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The crude product was purified by column chromatography on silica gel eluding with a solvent gradient of 100:0 changing to 90:10, by volume, hexane:ethyl acetate to afford tert-butyl 2-chloro-1H-benzimidizole-1-carboxylate as an oil. 1 H-NMR (CDCl3)delta: 7.95 (1H, m), 7.65 (1H, m), 7.35 (2H, m), 1.75 (9H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In toluene; | A mixture of methyl 3-(3-amino-4-(cyclohexyl(isobutyl)amino)phenyl)butanoate (100 mg, 0.29 mmol) and tert-butyl 2-chloro-IH-benzo[d]imidazole-1-carboxylate (109 mg, 0.43 mmol) in toluene (2 mL) was stirred at 110 C overnight. The mixture was cooled to room temperature, quenched with water (5 mL) and extracted with EtOAc (10 mL x 2). The combined organic layers were washed with brine (7 mL), dried over Na2SO4, and concentrated. The residue was purified by preparative TLC (20% EtOAc/PE) to give methyl 3-(3-((1 H-benzo[d]imidazol-2-yl)amino)-4-(cyclohexyl(isobutyl)amino)phenyl)butanoate (60 mg, 45% yield). LCMS (M+H):mz = 463.6. |
A101045 [221050-88-0]
tert-Butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate
Similarity: 0.64
A559474 [1092352-55-0]
tert-Butyl 2-chloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate
Similarity: 0.60
A436555 [849751-48-0]
tert-Butyl (2-chloropyrimidin-4-yl)carbamate
Similarity: 0.59
A317858 [857035-29-1]
Ethyl 2-chloro-1H-benzo[d]imidazole-6-carboxylate
Similarity: 0.58
A193100 [132873-77-9]
tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate
Similarity: 0.75
A343735 [1181267-36-6]
tert-Butyl 4-(1-(2-ethoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate
Similarity: 0.67
A144811 [374795-76-3]
tert-Butyl 5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate
Similarity: 0.65
A101045 [221050-88-0]
tert-Butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate
Similarity: 0.64
A334262 [1021918-86-4]
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole-1-carboxylate
Similarity: 0.64
A193100 [132873-77-9]
tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate
Similarity: 0.75
A343735 [1181267-36-6]
tert-Butyl 4-(1-(2-ethoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate
Similarity: 0.67
A334262 [1021918-86-4]
tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole-1-carboxylate
Similarity: 0.64
A763691 [1229000-10-5]
tert-Butyl 3-(1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate
Similarity: 0.60