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[ CAS No. 3705-87-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3705-87-1
Chemical Structure| 3705-87-1
Chemical Structure| 3705-87-1
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Product Details of [ 3705-87-1 ]

CAS No. :3705-87-1 MDL No. :MFCD00456409
Formula : C10H11ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :MAVNZJBNKICAAC-UHFFFAOYSA-N
M.W : 194.66 Pubchem ID :13061697
Synonyms :

Calculated chemistry of [ 3705-87-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.62
TPSA : 17.82 Ų

Pharmacokinetics

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) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 3.27
Log Po/w (MLOGP) : 2.5
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 2.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.45
Solubility : 0.0697 mg/ml ; 0.000358 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.14 mg/ml ; 0.000721 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0577 mg/ml ; 0.000296 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 3705-87-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P304+P340-P305+P351+P338-P405 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3705-87-1 ]

* 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.

  • Downstream synthetic route of [ 3705-87-1 ]

[ 3705-87-1 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 612-81-7 ]
  • [ 3705-87-1 ]
  • [ 206009-44-1 ]
  • 4
  • [ 3705-87-1 ]
  • 4'-(1-Isopropyl-1H-benzoimidazol-2-yl)-[2,3']biquinolinyl [ No CAS ]
  • 5
  • [ 123-51-3 ]
  • [ 6091-44-7 ]
  • [ 3705-87-1 ]
  • 2-[4-(5-Methyl-1H-imidazol-4-yl)piperidin-1-yl)-1-(1-methylethyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; dichloromethane; 3.7. 2-[4-(5-Methyl-1H-imidazol-4-yl)piperidin-1-yl]-1(1-methylethyl)-1H-benzimidazole. 34 ml (0.18 mole) of 5.3 N sodium methylate are added, under argon, to a suspension of 21.5 g (0.0904 mole) of the above compound in 100 ml of methanol. The mixture is stirred for 15 minutes and then concentrated under vacuum to two thirds its volume. 200 ml of dichloromethane are then added and sodium chloride is filtered off. The solution is concentrated under vacuum and the crystallized base is recovered. A solution of 400 ml of 3-methylbutan-1-ol and 8.8 g (0.0452 mole) of 2-chloro-l-(1-methylethyl)-1H-benzimidazole are then added. The mixture is heated at 120 C. by means of an oil bath for 24 hours. The precipitate of excess (6 g) <strong>[6091-44-7]<strong>[6091-44-7]piperidine</strong> hydrochloride</strong> (1:1) is filtered. The filtrate is evaporated to dryness and the residue is purified on a silica gel column eluding with a mixture of dichloromethane and methanol in proportions of 90:10 v/v. The pure fractions are combined and evaporated. The solid is washed with acetone and then dried under vacuum. 9.5 g of compound are obtained. Melting point: 258 C.
  • 6
  • [ 4857-06-1 ]
  • [ 67-68-5 ]
  • [ 3705-87-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In hexane; EXAMPLE 2 2-Chloro-1-(1-methylethyl)-1H-benzimidazole. 13.5 g (0.0885 mole) of 2-chloro-1H-benzimidazole, 9.2 ml of 1-bromo-1-methylethyl, 230 g of potassium carbonate and 200 ml of dimethyl sulphoxide are introduced into a round-bottom flask. The mixture is vigorously stirred for 4 hours while maintaining the temperature at 60 C. It is extracted several times with ether. The organic phases are combined and concentrated. The pasty residue is purified on a silica gel column eluding with a mixture of ethyl acetate and hexane in proportions of 20:80 v/v. The pure fractions are concentrated under vacuum. The residue is dissolved in 20 ml of hexane with the use of heat. The solution is cooled on a ice bath, the crystals are drained and then washed with a small amount of hexane and dried under vacuum. 12 g of compound are obtained. Melting point: 62 C.
  • 7
  • [ 6091-44-7 ]
  • [ 3705-87-1 ]
  • 2-[4-(1H-imidazol-4-yl)piperidin-1-yl]-1-(1-methyl-ethyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In dichloromethane; 4.7. 2-[4-(1H-imidazol-4-yl)piperidin-1-yl]-1-(1-methylethyl)-1H-benzimidazole. 47.3 ml (0.25 mole) of sodium methylate are added to a solution of 27.6 g (0.123 mole) of the above compound. The mixture is stirred for 15 minutes and it is, concentrated under vacuum to two thirds its volume, and 200 ml of dichloromethane are added. The sodium chloride precipitate which forms Is filtered. The filtrate is concentrated under vacuum. The crystallized residue is reacted with 12 g (0.061 mole) of 2-chloro-1-(1-methylethyl)-1H-benzimidazole in 60 ml of 3-riethybutan-1-ol at 120 C. for 36 hours. The precipitate of excess (8 g) <strong>[6091-44-7]piperidine</strong> monohydrochloride is filtered. The filtrate is evaporated to dryness. The residue obtained is purified on a silica gel column eluding with a mixture of dichloromethane and methanol in proportions ranging from 95:5 to 90:10 v/v. The pure fractions are combined and evaporated. The solid is washed with ether and dried under vacuum. 14.3 g of compound are obtained. Melting point: 183 C.
  • 8
  • [ 4857-06-1 ]
  • [ 75-26-3 ]
  • [ 3705-87-1 ]
YieldReaction ConditionsOperation in experiment
53.2% To a solution of 2-Chloro-1- isopropyl-1H-benzoimidazole (167.5 mg, 1.00 mmol) in DMF (4 mL) was added NaH (60% in mineral oil, 36 mg, 1.2 mmol) at 0 oC. After stirring 30 minutes at r.t., 2-Bromo-propane (244 mg, 1.20 mmol) was added dropwise and the reaction mixture was stirred at 37 oC for 12 hours. Then the reaction was quenched by water (30 mL) and extracted with EtOAc (50 mL x 3). The combined organic layer was washed with brine and dried over Na2SO4. The mixture was filtered and the filtrate solvent was removed under reduced pressure. The residue was purified via silica gel column chromatography (Petroleum ether/EtOAc) to give the title compound (105 mg, 53.2% yield) as a white solid. LC-MS: Calculated exact mass = 194.1; Found [M+H]+ =195.2; 197.2.
47% General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.
With potassium carbonate; In methanol; dichloromethane; dimethyl sulfoxide; EXAMPLE 13 6,7-Dimethoxy-2-[4-[1-(1-methylethyl)-1H-benzimidazol-2-yl]-1-piperazinyl]-4-quinazolinamine (Ia: R3 =1-(1-methylethyl)-1H-benzimidazol-2-yl; R4, R5, R6 and R9 =H; R7 and R8 =OMe; and n=1) A mixture of 2-chlorobenzimidazole (2.0 g), isopropyl bromide (1.36 ml) and potassium carbonate (34 g) in dimethyl sulfoxide (200 ml) was heated at 60 C. for 6 hr and poured into ice. The resulting mixture was extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed through silica gel using 5% methanol in dichloromethane. The appropriate fractions were evaporated to give 2-chloro-1-(1-methylethyl)benzimidazole, mp 58-60 C. Similarily, by replacing isopropyl bromide with propyl bromide, 2-chloro-1-propylbenzimidazole, nmr (CDCl3) delta 0.95 (t, 3H), 1.85 (m, 2H), 4.1 (t, 2H), 7.25 (m, 3H) and 7.65 (m, 1H), was obtained.
  • 9
  • [ 3705-87-1 ]
  • [ 60547-97-9 ]
  • 6,7-Dimethoxy-2-[4-[1-(1-methylethyl)-1H-benzimidazol-2-yl]-1-piperazinyl]-4-quinazolinamine [ No CAS ]
  • 6,7-dimethoxy-2-[4-(1-propyl-1H-benzimidazol-2-yl)-1-piperazinyl]-4-quinazolinamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; dichloromethane; butan-1-ol; A solution of 4-amino-6,7-dimethoxy-2-piperazinyl-quinazoline (12.05 g), <strong>[3705-87-1]2-chloro-1-(1-methylethyl)benzimidazole</strong> (6.55 g), triethylamine (21.5 ml) in butanol (600 ml) was refluxed for 72 hr and evaporated. The residue was chromatographed through silica gel using 10% methanol in dichloromethane and the appropriate fractions were evaporated to give a residue (5.37 g) of the title compound. The residue was crystallized from methanoldichloromethane: mp>250 C.; ir (CHCl3) 3520, 3410 and 1240 cm-1; uv max (MeOH) 250 (epsilon=67,500), 278 (epsilon=26,300), 282 (epsilon=26,000) and 342 (epsilon=6,750); nmr (CDCl3) delta 1.6 (d, 6H), 3.3 (s, 4H), 3.85 (s, 3H), 3.95 (s, 3H), 4.0 (m, 4H), 4.7 (m, 1H), 5.2 (s, 2H) and 7.2 (m, 6H); and Anal. Calcd. for C24 H29 N7 O2: C, 64.41% H, 6.53% N, 21.91% and Found: C, 64.04% H, 6.59% N, 21.86%. In the same manner, but replacing <strong>[3705-87-1]2-chloro-1-(1-methylethyl)benzimidazole</strong> with an equivalent amount of 2-chloro-1-propylbenzimidazole, the following compound of formula Ia was obtained; 6,7-dimethoxy-2-[4-(1-propyl-1H-benzimidazol-2-yl)-1-piperazinyl]-4-quinazolinamine: mp 250 C. (crystallized from dichloromethane-methanol); ir (nujol) 3440, 3320, 3210, 1645, 1245 and 1105 cm-1; uv max (MeOH) 341 (epsilon=6,650), 288 (epsilon=26,100), 278 (epsilon=26,100) and 250 nm (epsilon=66,700); and Anal. Calcd. for C24 H29 N7 O2: C, 64.41% H, 6.53% N, 21.91% and Found: C, 64.00% H, 6.53% N, 21.89%.
  • 10
  • [ 773837-37-9 ]
  • [ 3705-87-1 ]
  • [ 1263902-87-9 ]
YieldReaction ConditionsOperation in experiment
84% In N,N-dimethyl-formamide; at 100℃; for 2h; General procedure: 4 (8.7 mmol) was dissolved in dry DMF (15 mL), to the solution was added NaCN (9.2 mol), and the mixture was stirred for 2 h at 100 C. The mixture was poured into water (50 mL), filtrated, washed with water and dried to afford 5.
  • 11
  • [ 3705-87-1 ]
  • [ 2416-65-1 ]
YieldReaction ConditionsOperation in experiment
91.4% With thiourea; In ethanol; at 90℃; for 3h; To a solution of 2-Chloro-1- isopropyl-1H-benzoimidazole (1.3 g, 0.57 mmol) in EtOH (50 mL) was added thiourea (800 mg). The reaction mixture was stirred at 90 oC for 3 hours. The reaction mixture solvent was removed under reduced pressure and the residue was purified via column chromatography directly (Petroleum ether/EtOAc) to give title compound (1.02 g, 91.4% yield) as a yellow solid. LC-MS: Calculated exact mass = 192.1; Found [M+H]+ = 193.3.
  • 12
  • [ 3705-87-1 ]
  • 3-(1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)piperidine-2,6-dione [ No CAS ]
  • 13
  • [ 62-53-3 ]
  • [ 3705-87-1 ]
  • 1-isopropyl-N-(1-isopropyl-1H-benzo[d]imidazol-2-yl)-N-phenyl-1H-benzo[d]imidazol-2-amine [ No CAS ]
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