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[ CAS No. 2403-66-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2403-66-9
Chemical Structure| 2403-66-9
Chemical Structure| 2403-66-9
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Product Details of [ 2403-66-9 ]

CAS No. :2403-66-9 MDL No. :MFCD00022688
Formula : C10H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :CQFSGSFSOWEIGO-UHFFFAOYSA-N
M.W : 176.22 Pubchem ID :75470
Synonyms :

Calculated chemistry of [ 2403-66-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.84
TPSA : 48.91 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) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 2.49
Consensus Log Po/w : 1.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.05 mg/ml ; 0.00598 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 1.15 mg/ml ; 0.00651 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.05 mg/ml ; 0.000284 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 2403-66-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P322-P330-P332+P313-P337+P313-P340-P362-P363-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2403-66-9 ]

* 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 [ 2403-66-9 ]

[ 2403-66-9 ] Synthesis Path-Downstream   1~53

  • 2
  • [ 2403-66-9 ]
  • [ 74-86-2 ]
  • [ 117881-34-2 ]
  • 5
  • [ 110-87-2 ]
  • [ 2403-66-9 ]
  • 2-[3-(tetrahydropyran-2'-yloxy)propyl]-1H-benzimidazole [ No CAS ]
  • [ 649721-55-1 ]
  • 1-(tetrahydropyran-2'-yl)-2-[3'-(tetrahydropyran-2''-yloxy)propyl]-1H-benzimidazole [ No CAS ]
  • 6
  • [ 2403-66-9 ]
  • [ 24424-99-5 ]
  • tert-butyl 2-(3'-tert-butoxycarbonyloxypropyl)-1H-benzimidazole-1-carboxylate [ No CAS ]
  • 7
  • [ 2403-66-9 ]
  • [ 108-24-7 ]
  • [ 2403-67-0 ]
  • 3-(1'-acetyl-1'H-benzimidazol-2'-yl)propyl acetate [ No CAS ]
  • 8
  • [ 2403-66-9 ]
  • [ 100-39-0 ]
  • [ 121356-81-8 ]
  • 9
  • [ 2403-66-9 ]
  • [ 76-83-5 ]
  • 2-(3'-trityloxypropyl)-1H-benzimidazole [ No CAS ]
  • 10
  • [ 2403-66-9 ]
  • [ 7724-48-3 ]
  • 11
  • [ 2403-66-9 ]
  • [ 17341-93-4 ]
  • [ 866084-47-1 ]
  • 12
  • [ 2403-66-9 ]
  • 2-(3'-hydroxypropyl)benzimidazolium tetrachloroplatinate [ No CAS ]
  • 13
  • [ 2403-66-9 ]
  • 2-(3'-hydroxypropyl)benzimidazolium hexachloroplatinate [ No CAS ]
  • 14
  • [ 2403-66-9 ]
  • carbonic acid 3-(1<i>H</i>-benzoimidazol-2-yl)-propyl ester methyl ester [ No CAS ]
  • 15
  • [ 2403-66-9 ]
  • 3-(1H-benzimidazol-2-yl)-propan-1-acrylate [ No CAS ]
  • 16
  • [ 2403-66-9 ]
  • [ 866084-49-3 ]
  • 17
  • [ 2403-66-9 ]
  • [ 866084-50-6 ]
  • 18
  • [ 2403-66-9 ]
  • 2-(3-acryloyloxy-propyl)-benzoimidazole-1-carboxylic acid 2,2,2-trichloro-ethyl ester [ No CAS ]
  • 19
  • [ 2403-66-9 ]
  • methyl 4-[3'-(1'-benzyl-1'H-benzimidazol-2'-yl)propyloxy]benzoate [ No CAS ]
  • 20
  • [ 2403-66-9 ]
  • methyl 4-[3'-(1'-(tetrahydropyran-2''-yl)-1'H-benzimidazol-2'-yl)propyloxy]benzoate [ No CAS ]
  • 21
  • [ 2403-66-9 ]
  • [ 18162-48-6 ]
  • 2-(3-[tert-butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazole [ No CAS ]
  • 22
  • [ 20825-71-2 ]
  • [ 7440-44-0 ]
  • [ 95-54-5 ]
  • [ 2403-66-9 ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride; Step 1 3-(1H-Benzimidazol-2-yl)-propan-1-ol A mixture of 5.4 g of 1,2-phenylenediamine and 4.5 g of dihydro-furan-2-one in 50 mL of 4N hydrochloric acid was heated to reflux for 20 h, 1 teaspoon of decolorizing carbon added, and after another 15 min reflux, filtered hot. The filtrate was concentrated under reduced pressure to near dryness, the residue made basic (pH=8) with saturated sodium bicarbonate and extracted into 3*80 mL of ether. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. After drying under vacuum, 8.4 g of 3-(1H-benzimidazol-2-yl)-propan-1-ol was obtained as a solid.
In hydrogenchloride; Step 1 3-(1H-Benzimidazol-2-yl)-propan-1-ol: A mixture of 5.4 g of 1,2-phenylenediamine and 4.5 g of dihydro-furan-2-one in 50 mL of 4N hydrochloric acid was heated to reflux for 20 h, 1 teaspoon of decolorizing carbon added, and after another 15 min reflux, filtered hot. The filtrate was concentrated under reduced pressure to near dryness, the residue made basic (pH=8) with saturated sodium bicarbonate and extracted into 3*80 mL of ether. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. After drying under vacuum, 8.4 g of 3-(1H-benzimidazol-2-yl)-propan-1-ol was obtained as a solid.
  • 23
  • [ 110-87-2 ]
  • [ 2403-66-9 ]
  • [ 338467-35-9 ]
  • [ 107-13-1 ]
  • [ 338467-00-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; water; ethyl acetate; acetonitrile; Step 2 3-[2-(3-Hydroxy-propyl)-benzimidazol-1-yl]-propionitrile To a stirred solution of 3.8 g of <strong>[2403-66-9]3-(1H-benzimidazol-2-yl)-propan-1-ol</strong> and 4 g dihydropyran in 500 mL of THE was added p-toluenesulfonic acid monohydrate until the pH was about 3 (indicator paper). After stirring overnight, an additional 2 mL of dihydropyran was added: After 2 additional hours, the conversion was complete. The mixture was concentrated under reduced pressure and partitioned between 250 mL of 1N NaOH and 2*250 mL of ether. After drying over magnesium sulfate the combined extracts were concentrated to dryness. To a solution of the resulting crude oily 2-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-benzimidazole (14 g) in 250 mL of acetonitrile was added 5 mL of acrylonitrile, 2 drops of 1M tetrabutylammonium fluoride in THF and 1 drop 10N NaOH. After heating to 85 C. for 16 h, conversion was complete (TLC elution with 90:10 methylene chloride:methanol). After concentration under reduced pressure, the residue was partitioned between 2*200 mL of ethyl acetate and 200 mL of water. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude 3-(2-[3-(tetrahydro-pyran-2-yloxy)-propyl]-benzimidazol-1-yl}-propionitrile was stirred in 250 mL of methanol with sufficient p-toluenesulfonic acid monohydrate to make the solution acidic (pH=1-2). After stirring overnight, the solution was concentrated under reduced pressure, made basic (pH=8) with 1N sodium hydroxide and extracted into 8*50 mL of ethyl acetate. The aqueous layer was saturated with NaCl to aid in extraction of the product. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography using a gradient of ethyl acetate, then 10% methanol in ethyl acetate, followed by trituration with ether-hexane gave 4.8 g of 3-[2-(3-hydroxy-propyl)-benzimidazol-1-yl]-propionitrile as a solid.
  • 24
  • [ 2403-66-9 ]
  • [ 74-88-4 ]
  • [ 116040-91-6 ]
YieldReaction ConditionsOperation in experiment
Methyl Iodide (839muL, 13.48 mmol) was added to a mixture of the 3-(lH-benzimidazol- 2-yl)propan-l-ol (2.5g, 14.19 mmol) and Et3N (2.16mL, 15.6 mmol) in DCM (100 mL) at O0C. The reaction stirred for 40 minutes, was warmed to room temperature and stirred 1 hour. DMF (50 mL) was added and continued stirring for 1 hour. Cesium carbonate (4.62g, 14.19 mmol) and methyl iodide (839muL, 13.48 mmol) were added and the reaction stirred overnight. The reaction was diluted with EtOAc, washed with water, saturated sodium bicarbonate and brine. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude solids were triturated with ethyl ether/hexane (1 :2) to give the title compound (1-21: step 1) as a solid. Data for 1-21: step 1: ESI+ MS: 191.1[MH]+.
  • 25
  • [ 10025-99-7 ]
  • [ 2403-66-9 ]
  • bis(2-(3'-hydroxypropyl)benzimidazolium) hexachloroplatinate [ No CAS ]
  • 26
  • [ 10025-99-7 ]
  • [ 2403-66-9 ]
  • bis(2-(3'-hydroxypropyl)benzimidazolium) tetrachloroplatinate [ No CAS ]
  • 27
  • [ 2403-66-9 ]
  • [ 307931-43-7 ]
  • (1R,2R)-2-(4-[2-(3-hydroxypropyl)-1H-benzimidazol-1-yl]methyl}phenyl)cyclohexane-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 28
  • [ 2403-66-9 ]
  • [ 24424-99-5 ]
  • [ 405174-00-7 ]
  • 29
  • [ 627-00-9 ]
  • [ 95-54-5 ]
  • [ 2403-66-9 ]
  • 31
  • [ 615-28-1 ]
  • [ 2403-66-9 ]
  • 32
  • [ 95-54-5 ]
  • [ 2403-66-9 ]
  • 33
  • 3-(1H-Benzoimidazol-2-yl)-propan-1-ol; hydrochloride [ No CAS ]
  • [ 2403-66-9 ]
  • 37
  • [ 2403-66-9 ]
  • [ 104-15-4 ]
  • [ 1617532-01-0 ]
YieldReaction ConditionsOperation in experiment
57% With dmap; triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; for 4h; To a solution (3 mL / 3 mL) of anhydrous methylene chloride and tetrahydrofuran in a 1: 1 mixture was added 2- (3-hydroxypropyl) -benzyl(119 mg, 624 [mu] mol), 4-dimethylaminopyridine (DMAP; 3.50 mg,28.4 mumol) and triethylamine (57.4 mg, 568 mumol) were placed at 0 C. The mixture was stirred at room temperature for 4 hours, brine, methyleneChloride and distilled water. The separated organic layer was dried over anhydrous magnesium sulfate and then decompressed to remove the solvent. The mixture was purified by flash column chromatography (EtOAc: Hex = 4: 1, Rf = 0.4) to give the title compound (106 mg,57%, colorless oil).
  • 38
  • [ 2403-66-9 ]
  • (±)-(3S,4S)-3-(2-((3-(1-p-toluenesulfonyl-1H-benzo[d]imidazol-2-yl)propyl)(cyclopropyl)amino)ethyl)-7-fluoro-4-isopropylchroman-3-ol [ No CAS ]
  • 39
  • [ 2403-66-9 ]
  • (±)-(3S,4S)-3-(2-((3-(1-p-toluenesulfonyl-1H-benzo[d]imidazol-2-yl)propyl)(2,2,2-trifluoroethyl)amino)ethyl)-7-fluoro-4-isopropylchroman-3-ol [ No CAS ]
  • 40
  • [ 2403-66-9 ]
  • (±)-(3S,4S)-3-(2-((3-(1H-benzo[d]imidazol-2-yl)propyl)(cyclopropyl)amino)ethyl)-7-fluoro-4-isopropylchroman-3-ol [ No CAS ]
  • 41
  • [ 2403-66-9 ]
  • (±)-(3S,4S)-3-(2-((3-(1H-benzo[d]imidazol-2-yl)propyl)(2,2,2-trifluoroethyl)amino)ethyl)-7-fluoro-4-isopropylchroman-3-ol [ No CAS ]
  • 43
  • [ 2403-66-9 ]
  • [ 106-95-6 ]
  • 3-(1-allyl-1H-benzo[d]imidazol-2-yl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% at 150℃; for 0.0333333h;Microwave irradiation; The benzimidazole was dissolved in acetonitrile. Allyl bromide (1.1 equiv) was added and the mixture was heated in the microwave to 150 C for 2 minutes. Celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.
26% In acetonitrile; at 150℃; for 0.0333333h;Microwave irradiation; General procedure: The benzimidazole was dissolved in acetonitrile. Allyl bromide (1.1 equiv) was added and the mixture was heated in the microwave to 150 C for 2 minutes. Celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.
  • 44
  • [ 2403-66-9 ]
  • [ 920-46-7 ]
  • 2-(3-methacryloyloxypropyl)benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3h; In a 300 ml recovery flask, 17.62 g (100.0 mmol) of 2- (3-hydroxypropyl) benzimidazole,22.26 g (220.0 mmol) of triethylamine, 0.22 g (1.0 mmol) of 3,5-di-tert-butyl-4-hydroxytoluene and 200 ml of tetrahydrofuran were added to prepare a reaction solution. After the reaction solution was cooled to 0 C., 23.00 g (220.0 mmol) of methacryloyl chloride was added dropwise and the mixture was stirred at room temperature for 3 hours, and the precipitated triethylamine hydrochloride was filtered off.Then, the filtrate was concentrated and 200 ml of methanol and 0.54 g (10.0 mmol) of sodium methoxide were added to the solution to prepare a solution, and the mixture was stirred at room temperature for 1 hour. Subsequently, this solution was concentrated and extraction operation with 100 ml of ethyl acetate was carried out three times, and the extracted solutions were mixed and concentrated to obtain a dry matter. This dry matter was dissolved in ethyl acetate 10 mlAnd 10 ml of hexane to obtain 14.48g (yield: 59%) of white crystals.
  • 45
  • [ 2403-66-9 ]
  • [ 939-26-4 ]
  • 1,3-bis(naphthalen-2-ylmethyl)-2-(3-hydroxypropyl)-1H-benzimidazol-3-ium bromide [ No CAS ]
  • 46
  • [ 2403-66-9 ]
  • [ 939-26-4 ]
  • 3-(1-(naphthalen-2-ylmethyl)-benzimidazol-2-yl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% 3-(Benzimidazol-2-yl)propan-1-ol (1.99 g, 11.3 mmol) was dissolved in acetonitrile (57 mL) potassium hydroxide (0.718 g, 12.8 mmol) was added, and the mixture was refluxed for 30 min. 2-(Bromomethyl)naphthalene (2.50 g, 11.3 mmol) was added and the mixture was refluxed for 30 min. The reaction mixture was filtered hot to remove a white solid, presumed to be potassium bromide. The resulting filtrate was slowly evaporated to yield crystalline material. The crystals were washed in ether (20 mL), collected via vacuum filtration and air dried to yield a white powder SI-3 (1.85 g, 51%). Mp: 126 - 127 C. Anal. Calcd for C21H20N2O: C, 79.72; H, 6.37; N, 8.85%. Found: C, 79.79; H, 6.39; N, 8.85%. 1H NMR (500 MHz, DMSO- d6) 7.89 - 7.87 (m, 2H), 7.83 - 7.80 (dd, 1H, J = 6.0, 3.4 Hz), 7.61 - 7.57 (m, 2H), 7.51 - 7.45 (m, 3H), 7.27 (dd, 1H, J = 8.5, 1.8 Hz), 7.18 - 7.10 (m, 2H), 5.65 (s, 2H), 4.57 (s, 1H), 3.50 (q, 2H, J = 6.1 Hz), 2.94 (t, 2H, J = 7.6 Hz), 1.94 (dt, 2H, J = 6.8 Hz). 13C{1H} NMR (125 MHz, DMSO-d6) 155.3, 142.3, 135.3, 134.6, 132.8, 132.2, 128.4, 127.6, 126.4, 124.8, 124.6, 121.6, 121.3, 118.4, 110.1, 60.0, 46.2, 30.2, 23.4.
  • 47
  • [ 2403-66-9 ]
  • 2-(3-hydroxypropyl)-1-(naphthalen-2-ylmethyl)-3-(quinolin-2-ylmethyl)benzimidazolium bromide [ No CAS ]
  • 48
  • [ 2403-66-9 ]
  • 2-(3-hydroxypropyl)-1,3-bis(quinolin-2-ylmethyl)benzimidazolium chloride [ No CAS ]
  • 49
  • [ 4377-41-7 ]
  • [ 2403-66-9 ]
  • C20H19N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
3-(Benzimidazol-2-yl)propan-1-ol (0.40 g, 2.27 mmol) was dissolved in acetonitrile (11 mL) potassium hydroxide (0.15 g, 2.67 mmol) was added, and the mixture was refluxed for 30 min. 2-(Chloromethyl)quinoline (0.40 g, 2.26 mmol) was added, and the mixture was refluxed overnight.
  • 50
  • [ 2403-66-9 ]
  • 6-chloro-N-[(2,4-dimethylthiazol-5-yl)methyl]-5-methyl-2-methylsulfonylpyrimidin-4-amine [ No CAS ]
  • [ 1370510-22-7 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hexamethyldisilazane; In tetrahydrofuran; 6-chloro-N-[(2,4-dimethylthiazol-5-yl)methyl]-5-methyl-2-methylsulfonyl-pyrimidin-4-amine F5 (480 mg, 1.384mmol) and <strong>[2403-66-9]3-(1H-benzimidazol-2-yl)propan-1-ol</strong> (244 mg, 1.38 mmol) were placed in a 20 mL vial and dissolved in THF(5 mL). AIM solution of NaHMDS in THF (1.38 mL, 1.38 mmol) was added, and the reaction was stirred overnight.Solvent was then removed, and the product was purified by silica gel flash column chromatography (EtOAc/hexanesgradient). 500 mg (82%) of F6 were isolated as an off-white foam. 1H NMR delta (300 MHz, DMSO-d6): 7.84-7.80 (1 H, m),7.76 (2 H, dd, J = 6.20, 3.18 Hz), 7.51 (2 H, dd, J = 6.28, 3.15 Hz), 4.46 (2 H, d, J = 5.76 Hz), 4.37-4.31 (2 H, m), 2.54(4H, s), 2.46 (3 H, s), 2.29 (3 H, s), 1.99 (3 H, s). HRMS (Electrospray): m/z 443.1413 (MH+).
  • 51
  • [ 2403-66-9 ]
  • 1-[3-(1-methyl-1H-benzimidazol-2-yl)propyl]-N-[2-(1H-pyrrol-1-yl)phenyl]-L-prolinamide bis(trifluoroacetic acid) salt [ No CAS ]
  • 52
  • [ 2403-66-9 ]
  • [ 916143-44-7 ]
  • 53
  • [ 2403-66-9 ]
  • [ 52462-29-0 ]
  • [ 186407-74-9 ]
  • C27H30Cl2N4ORu(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; ethylenediamine; triethylamine; sodium hydroxide; In ethylene glycol; at 50℃; for 5h;Inert atmosphere; Weigh 182 mg of <strong>[2403-66-9]2-(3-hydroxypropyl)benzimidazole</strong> and 120 mg of 6-bromocarbazole.And 31.5mg of dichloro-di-methylisopropylbenzene dioxalate dichloride dissolved in 15ml of ethylene glycol,0.2 ml of NaOH was added dropwise with stirring.0.1 ml of ethylenediamine,Add 3 mg of cesium carbonate,0.2 ml of triethylamine,Passing nitrogen,Heat to 50 degrees,After 5 hours,Add 1 mg of zinc chloride and 1 ml of hydrochloric acid.Precipitating a red solid,That is, the product is dichloro-(2-(3-hydroxypropyl)-1-oxazolylbenzimidazolyl)-methylisopropylbenzene ruthenium (II).
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