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CAS No. : | 1008361-81-6 | MDL No. : | MFCD12828061 |
Formula : | C7H4BrClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MJXDWVUPIRXRDE-UHFFFAOYSA-N |
M.W : | 231.48 | Pubchem ID : | 59474483 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.8 |
TPSA : | 28.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.72 cm/s |
Log Po/w (iLOGP) : | 1.63 |
Log Po/w (XLOGP3) : | 2.81 |
Log Po/w (WLOGP) : | 2.98 |
Log Po/w (MLOGP) : | 2.32 |
Log Po/w (SILICOS-IT) : | 3.35 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.65 |
Solubility : | 0.0517 mg/ml ; 0.000223 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.07 |
Solubility : | 0.197 mg/ml ; 0.000852 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.39 |
Solubility : | 0.00952 mg/ml ; 0.0000411 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
90% | With camphorsulfonic acid In tetrahydrofuran for 16h; Reflux; | 13.2 step 2: To a solution of 128 (22 g, 0.095 mol) in dry THF (660 mL) was added 3,4-dihydro-2H-pyran (24 g, 0.286 mol) and camphorsulfonic acid (2.2 g, 0.00948 mol) and the solution was heated to reflux for 16 h. The resulting mixture was concentrated, and the residue obtained was purified by Si02 chromatography eluting with 20% EtO Ac/petroleum ether to afford 27 g (90%) of 5-bromo-4-chloro-l- (tetrahydro-pyran-2-yl)-lH-benzoimidazole (130) as pale yellow solid. |
27 g | With camphor-10-sulfonic acid In tetrahydrofuran at 60℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 1.5h;Reflux; | Example 13 N2 -[(4-Chloro-lH-benzimidazol-5-yl)methyl]- N4 -(5-cyclopropyl-lH-pyrazol-3-yl)pyrimidine-2,4- diamine (1-3) step 1 : A mixture of 4-bromo-3-chloro-benzene-l,2-diamine (CASRN 1008361-80-5, 27 g, 0.1221 mol) and formic acid (80 mL) was heated to reflux for 1.5 h. After the completion of the reaction, 10% NaOH was added until the solution basic. The resulting solid was filtered and washed well with water then dried over night over suction to afford 22 g (78%) of 5-bromo-4-chloro-lH-benzoimidazole (128) as pale yellow solid which was used without additional purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr | ||
Multi-step reaction with 3 steps 1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3: nickel; hydrogen; ammonia / methanol / 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr 4: N-ethyl-N,N-diisopropylamine / butan-1-ol / 140 °C / Sealed tube 5: toluene-4-sulfonic acid / methanol / 100 °C / Sealed tube | ||
Multi-step reaction with 5 steps 1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3: nickel; hydrogen; ammonia / methanol / 16 h 4: N-ethyl-N,N-diisopropylamine / butan-1-ol / Sealed tube 5: toluene-4-sulfonic acid / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr 4: N-ethyl-N,N-diisopropylamine / butan-1-ol / 140 °C / Sealed tube | ||
Multi-step reaction with 4 steps 1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3: nickel; hydrogen; ammonia / methanol / 16 h 4: N-ethyl-N,N-diisopropylamine / butan-1-ol / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr 4: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C | ||
Multi-step reaction with 4 steps 1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3: nickel; hydrogen; ammonia / methanol / 16 h 4: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3.1: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 20 °C 5.2: 0 - 20 °C | ||
Multi-step reaction with 5 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3.1: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 20 °C 5.2: 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C | ||
Multi-step reaction with 6 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: camphorsulfonic acid / tetrahydrofuran / 16 h / Reflux 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C / Inert atmosphere 3.1: ammonia; hydrogen / methanol / 16 h / 3750.38 Torr 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 20 °C 5.2: 0 - 20 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 96 h / 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 23 °C 7.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 23 °C 7.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 23 °C 7.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / Sealed tube 8.1: toluene-4-sulfonic acid / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: camphor-10-sulfonic acid / tetrahydrofuran / 16 h / 60 °C 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 6 h / 110 °C 3.1: nickel; hydrogen; ammonia / methanol / 16 h 4.1: sodium hydroxide / tetrahydrofuran; water / 16 h / 0 - 23 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.42 h / 0 - 23 °C 5.2: 6 h / 0 - 23 °C 6.1: hydrogenchloride / 1,4-dioxane; methanol / 2 h / 23 °C 7.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / Sealed tube 8.1: toluene-4-sulfonic acid / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 120℃; for 0.583333h; Inert atmosphere; Microwave irradiation; | 9 (2S,4R)-l-(2-(3-Acetyl-lH-indazol-l-yl)acetyl)-4-fluoro-N-(2-fluoro-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine-2-carboxamide (0.142 g) (S3), 2-bromo- 6-chloro-7H-purine (0.050 g) (S2), Pd(dppf)Cl2 (35 mg) and potassium carbonate (0.148 g) were taken up in a pressure tube under argon. To this mixture, 4 mL of dioxane and 1 mL of water were added. The mixture was bubbled with argon for 5 min and the vial was stoppered and subjected to microwave irradiation at 100 °C for 45 min. The volatiles were removed under reduced pressure and the residue was purified by ISCO (0-5 % MeOH in CH2CI2) to afford the desired product. 1H NMR (400 MHz, DMSO) (major rotamer) δ 2.12-2.32 (m, 1H), 2.54-2.64 (m, 1H), 2.61 (s, 3H), 3.96-4.08 (m, 1H), 4.25 (dd, J = 12.8, 21.8 Hz, 1H), 4.75 (t, J = 8.6 Hz, 1H), 5.57 (d, J = 53.6 Hz, 1H), 5.59 (d, J = 17.2 Hz, 1H), 5.80 (d, J = 17.2 Hz, 1H), 7.27 (t, J = 8 Hz, 1H), 7.34 (t, J = 8 Hz, 1H), 7.48 (t, J = 7.2 Hz, 1H), 7.70 (d, J = 8.5 Hz, 1H), 7.76 (t, J = 7.4 Hz, 1H), 7.92 (t, J = 7.2 Hz, 1H), 8.18 (d, J = 8.2 Hz, 1H), 8.71 (s, 1H), 10.00 (s, 1H), 14.00 (s, 1H). 19F- MR (DMSO-de ) (major rotamer): δ -126.2, -175. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
746 mg | Stage #1: 6-bromo-7-chloro-3H-imidazo[4,5-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; | 162 Preparation 162: 6-Bromo-7-chloro-1-methyl-1H-1,3-benzodiazole To a solution of 5-bromo-4-chloro-1H-1,3-benzodiazole (5 g, 21 .60 mmol) in DMF (50.2 mL, 648 mmol) at 0°C was added NaH (60 wt% in mineral oil, 1.123 g, 28.1 mmol). The reaction mixture was warmed to RT over 30 mm then iodomethane (1.486 mL, 23.76 mmol) was added. The reaction mixture wasstirred at RT for 3 h, before addition of sat. aq. NH4CI (200 mL) and extraction with DCM (3 x 50 mL). The combined organic phase was washed with sat. aq. NH4CI (100 mL), water (100 mL), and 1M aq.LiCI (100 mL) then dried (MgSO4) and concentrated. The residue was purified by column chromatography on NH silica gel (gradient elution, 0-30%, EtOAc/iso-hexanes), to give the title compound (746 mg). MS: [M+H] = 245. |
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