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[ CAS No. 152628-02-9 ]

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CAS No. :152628-02-9 MDL No. :MFCD03840857
Formula : C19H20N4 Boiling Point : 584.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :304.39 g/mol Pubchem ID :9796488
Synonyms :

1. TELMISARTAN IMPURITY A

Safety of [ 152628-02-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
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Application In Synthesis of [ 152628-02-9 ]

  • Upstream synthesis route of [ 152628-02-9 ]
  • Downstream synthetic route of [ 152628-02-9 ]

[ 152628-02-9 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 25148-68-9 ]
  • [ 152628-03-0 ]
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YieldReaction ConditionsOperation in experiment
77.4%
Stage #1: at 70 - 135℃; for 13.5 h;
Stage #2: With ammonia In water at 30 - 90℃; for 1 h;
4-Methyl-2-n-propyl-lH-benzimidazole-6-carboxylic acid (50 gms) is suspended in Poly phosphoric acid (300 gms), temperature is raised and maintained for 30 min at 70 - 750C, N-Methyl-o-phenylenediamine dihydrochloride. (45 gms) is added lot wise over 2 hrs and maintained at temperature of 70 - 750C for lhr. The temperature of the reaction mass is raised and maintained for 10 hrs at 130 - 1350C. Mass temperature is cooled to 7O0C, water (600 ml) is added slowly at temperature of 60 - 9O0C. Temperature of the reaction mass is cooled to 3O0C, pH is adjusted to 8.0 - 8.5 with aqueous ammonia solution. EPO <DP n="12"/>Temperature of the reaction mass is raised, maintained at 50- 550C for 1 hr, filter the solid, wet cake is washed with hot water (200 ml) and unload the wet cake. The above wet cake suspended in water (900 ml), temperature is raised and mixed for 1 hr at 50 - 550C. Filtered the solid, washed with hot water (100 ml) and dried the wet cake at temperature of 70 - 750C till constant weight. The above dry material is suspended in methanol (260 ml), and temperature is raised to 45 - 5O0C, charcoal (6.5 gms) is added and mixed for about 30 min. Insolubles are filtered through hyflow bed, washed the bed with hot methanol (60 ml), collect and cooled the filtrate to 250C. Water (160 ml) is added slowly to the filtrate at temperature of 25 - 350C, Mass temperature is raised, maintained for 1 hr at reflux temperature. Reaction mass temperature is cooled, maintained for 2 hrs at 0 - 50C. The solid obtained is filtered, wet cake is washed with methanol (60 ml), the wet cake is dried at temperature of 70 - 750C till becomes constant weight. The dry weight of 4-Methyl-6(l -methyl benzimidazol-2-yl)-2-n-propyl IH- benzimidazole is 54 gms (Yield 77.4percent). Water content by KF is 5.85percent.
Reference: [1] Patent: WO2007/10558, 2007, A1, . Location in patent: Page/Page column 5; 10-11
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 2
  • [ 4760-34-3 ]
  • [ 152628-03-0 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 75 - 145℃;
Stage #2: With sodium hydroxide In water
Example 2; Variant 2; Methanesulphonic acid is heated to about 80° C. At a temperature of 75° C. to 85° C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85° C. to 95° C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110° C. to 130° C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160° C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145° C. It is cooled to <100° C. and water is metered into the reaction mixture. 50percent sodium hydroxide solution is added at <100° C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100° C.At a temperature of <80° C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40° C. for technical reasons and the product is isolated.Yield: 78-90percent of theoryHPLC purity: >99.5percent.
Reference: [1] Patent: US2011/190508, 2011, A1, . Location in patent: Page/Page column 2
[2] Journal of Chemical Research, 2010, # 2, p. 95 - 97
[3] Synthetic Communications, 2009, vol. 39, # 23, p. 4149 - 4157
[4] Patent: JP2015/160810, 2015, A, . Location in patent: Paragraph 0051; 0052
  • 3
  • [ 1345840-05-2 ]
  • [ 123-72-8 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
85% With sodium dithionite In methanol; water for 12 h; Reflux The compound 11 (40 g, 0.14 mol) and sodium dithionite (148 g, 0.84 mol) was suspended in a mixture of methanol (320 ml) and water (320 ml), butyl aldehyde (256 ml, 0.28 mol) was added, then the stirred mixture was heated at reflux for 12 h. After cooling, the reaction mixture was poured slowly into water (2400 ml) with stirring. The resultant suspension was filtered and the collected solid washed with water, and crystallized from toluene to give bis-benzimidazole 4 (36.5 g, 85percent) as light yellow solid; mp: 138-139 °C; 1H NMR (400 MHz, DMSO-d6) δ 0.97 (t, J=6.8 Hz, 3H, CH3), 1.83 (m, 2H, CH2), 2.59 (s, 3H, CH3), 2.85 (t, J=4.5 Hz, 2H, CH2), 3.89 (s, 3H, NCH3), 7.23-7.27 (m, 2H, ArH), 7. 44 (s, br, 1H, ArH), 7.56 (d, J=6.8 Hz, 1H, ArH), 7.68 (d, J=6.8 Hz, 1H, ArH), 7.78 (br s, 1H, ArH); 13C NMR (100 MHz, DMSO-d6) δ 13.7, 16.8, 21.1, 30.6, 31.7, 110.3, 118.6, 121.7, 121.9, 122.9, 123.2, 136.6, 142.5, 154.3, 156.2; MS (+C, ESI): M=304, found 305 [M+H]+; HRMS (ESI): [M+H]+ calcd for C19H21N4: 305.1688, found 305.1754.
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 4
  • [ 4760-34-3 ]
  • [ 152628-00-7 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
62% at 150℃; for 12 h; A mixture of methyl 4-methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylate 2 (10 mmol) and N-methyl-o-phenylenediamine (10 mmol) in PPA (20 ml) were taken in a two necked flask fitted with a condenser and the reaction mixture was refluxed at 150 FontWeight="Bold" FontSize="10" °C for 12 h. After the completion of the reaction, the mixture was poured into water and the pH was adjusted to 9 using ammonium hydroxide. The mixture was extracted with ethyl acetate (50 mL x 3)and the combined organic phase was washed with brine (50 mL), dried over sodium sulphate and concentrated under vacuum. The crude mixture was purified by column chromatography using CHCl3-MeOH (9.3:0.7) to give the product 1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole (3). 1,7'-Dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazole 3. Yield 62percent; m.p. 128-130 °C (lit 138-139 °C); IR (KBr): 3310 (N-H), 2928 (C-H), 1628 (C=C), 1284 (N-N) cm-1; 1H NMR (CDCl3, 400 MHz): δ 7.89 (s, 1H, Ar-H), FontWeight="Bold" FontSize="10" 7.62 (t, J=6.8 Hz, 2H, Ar-H), 7.31 (s, 1H, Ar-H), 7.24 (m, 2H, Ar-H), 5.57 (s, 1H, N-H), 3.92 (s, 3H, N-CH3), 3.16 (t, J=7.6 Hz, 2H, CH2), 2.66 (s, 3H, Ar–CH3), 1.94 (m, 2H, CH2), 1.12 (t, J=7.6Hz,3H, CH3); 13C NMR (CDCl3, 100M Hz): δ 153.3,151.4, 142.7, 139.3, 138.4, 136.4, 126.7, 124.1, 123.9, 123.0, 122.1, 119.5,111.2, 110.0, 31.9, 31.8, 21.6, 16.5, 13.9; MS (ESI): m/z 305 (M+1); Anal.Calcd for C19H20N4: C, 74.97; H, 6.22; N,18.41. Found: 75.05; H, 6.29; N, 18.49percent.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2589 - 2593
  • 5
  • [ 81684-80-2 ]
  • [ 152628-03-0 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 70 - 130℃;
Stage #2: With ammonia In water; ethyl acetate for 3 h; Cooling with ice
Example 1:Orthophosphoric acid (210 gms) was taken in round bottomed flask and Ρ205 (210 gms) was added in portions with vigorous stirring. (Note: Sharp increase in temperature > 200 °C). The above mass is allowed to cool to 70 °C and 2-n-propyl- 4-methyl-benzimidazole-6-carboxylic acid (70 gms, 0.321 mol) was added slowly. Then N-methylbenzene-l,2-diamine hydrochloride (62.3 gms, 0.321 mol) was added in small portions at same temperature and then the temperature was raised to 125-130 °C. After completion, reaction was quenched with ice cold water (1 Lt), adjusted pH of the reaction mixture to 9-10 by the addition of aqueous ammonia solution. Obtained solid was filtered and washed with cold water until the pH of the filtrate becomes neutral. Then the crude solid was washed with hot water until colorless filtrate was observed. The crude solid was boiled in ethyl acetate (700 ml) for 2-3 hrs. The reaction mass was cooled and the suspension was filtered off and dried to yield 2-n-propyl-4-methyl-6-(l-methylbenzimidazol-2-yl)-lH- benzimidazole (V) (80 gms, Yield : 82 percent).
Reference: [1] Patent: WO2012/28925, 2012, A2, . Location in patent: Page/Page column 19
[2] Patent: WO2006/44754, 2006, A2, . Location in patent: Page/Page column 26
  • 6
  • [ 152628-01-8 ]
  • [ 152628-02-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[2] Patent: WO2012/28925, 2012, A2,
[3] Patent: WO2012/28925, 2012, A2,
[4] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 7
  • [ 18595-14-7 ]
  • [ 152628-02-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[2] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 8
  • [ 301533-59-5 ]
  • [ 152628-02-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[2] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 9
  • [ 152628-00-7 ]
  • [ 152628-02-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[2] Patent: WO2012/28925, 2012, A2,
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 10
  • [ 884330-17-0 ]
  • [ 152628-02-9 ]
Reference: [1] Patent: WO2006/44754, 2006, A2, . Location in patent: Page/Page column 30
  • 11
  • [ 884330-18-1 ]
  • [ 152628-02-9 ]
Reference: [1] Patent: WO2006/44754, 2006, A2, . Location in patent: Page/Page column 31
  • 12
  • [ 675882-71-0 ]
  • [ 152628-02-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[2] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 13
  • [ 81684-80-2 ]
  • [ 152628-03-0 ]
  • [ 884330-09-0 ]
  • [ 884330-18-1 ]
  • [ 884330-17-0 ]
  • [ 152628-02-9 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 1, p. 81 - 85
  • 14
  • [ 107-92-6 ]
  • [ 152628-02-9 ]
Reference: [1] Journal of Molecular Structure, 2017, vol. 1147, p. 121 - 128
  • 15
  • [ 1345840-14-3 ]
  • [ 152628-02-9 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 16
  • [ 1345840-21-2 ]
  • [ 152628-02-9 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 17
  • [ 15174-69-3 ]
  • [ 152628-02-9 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 18
  • [ 54674-91-8 ]
  • [ 152628-02-9 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 19
  • [ 861792-67-8 ]
  • [ 152628-02-9 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 20
  • [ 95-48-7 ]
  • [ 152628-02-9 ]
Reference: [1] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
  • 21
  • [ 668276-43-5 ]
  • [ 152628-02-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2589 - 2593
  • 22
  • [ 152628-02-9 ]
  • [ 150766-86-2 ]
  • [ 144701-48-4 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 1 h;
Stage #2: at 10℃;
The compound of formula I (10 g, 1 eq) was added to DMF (50 ml) and stirred to dissolve, And then cooled to 0-5 ° C, 55percent NaH (3.4 g, 2.5 eq) was added slowly, After the addition, the mixture was stirred at the same temperature for about 1 hour, The temperature of the reaction solution is controlled to 10 degrees or less, The title compound of Example 6 (9.5 g) was dissolved in DMF (10 ml) Slowly dripping, stirring at this temperature for 1-2 hours, TLC or HPLC detection of raw materials after the basic reaction is complete, The temperature maintained at 10 degrees below the addition of dilute hydrochloric acid to adjust the pH value of the solid precipitation, Stirring, the resulting solid filtration, washing, After drying, telmisartan (15.2 g) was obtained in a yield of 95percent.
Reference: [1] Patent: CN104768936, 2017, B, . Location in patent: Paragraph 0116-0117; 0119; 0137; 0139
  • 23
  • [ 667457-41-2 ]
  • [ 152628-02-9 ]
  • [ 144701-48-4 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5 h; Cooling with ice
Stage #2: at 20 - 50℃; for 5 h;
60percent NaH (1.0 g, 0.025 mol) was added to DMF (10 mL) The mixture was stirred under ice-water and the compound of formula I (3.05 g, 0.01 mol) was added, The mixture was stirred at room temperature for 30 minutes. The title compound (II) (2.46 g, 0.01 mol) of Example 1 was dissolved in DMF (10 mL) and slowly added to the above reaction solution, Stirred at room temperature for 1 hour; heated to 50 ° C for 4 hours, TLC detection reaction ends. The reaction solution was poured into ice water (100 mL), stirred, With concentrated hydrochloric acid to adjust the pH to solid precipitation; filter, the resulting filter with water once, Dried to give a solid brown telmisartan (4.3 g, yield 84percent).
Reference: [1] Patent: CN104768936, 2017, B, . Location in patent: Paragraph 0108-0109; 0111
  • 24
  • [ 152628-02-9 ]
  • [ 144701-48-4 ]
YieldReaction ConditionsOperation in experiment
75.1%
Stage #1: With potassium hydroxide In acetonitrile for 0.166667 h;
Stage #3: With hydrogenchloride In water
The compound of formula I (0.62 g, 1 eq) was added to acetonitrile (10 ml) and stirred well. KOH (0.14 g, 1.1 eq) was added slowly, stirred for about 10 minutes, The title compound of Example 10 was added (II, R = COOCH3) (0.5 g, 1 eq) was slowly added, and after stirring for 3-4 hours, TLC After the reaction was complete, 50percent ethanol (30 mL) was added directly, The reaction was refluxed for 6 hours. After the TLC test reaction was complete, the organic solvent was recovered under reduced pressure, The remaining solution was added dropwise with hydrochloric acid (1: 1) to pH neutral. There are solid precipitation, filtration, washing, extraction of telmisartan crude, Recrystallization of telmisartan (yield 75.1percent), liquid purity greater than 98percent.
Reference: [1] Patent: CN104768936, 2017, B, . Location in patent: Paragraph 0126-0127
  • 25
  • [ 136304-93-3 ]
  • [ 152628-02-9 ]
  • [ 144701-48-4 ]
YieldReaction ConditionsOperation in experiment
120 g
Stage #1: With sodium hydroxide In water for 0.166667 h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In water at 80 - 85℃; for 4 h;
Stage #3: With sodium hydroxide In butan-1-ol at 123 - 126℃; for 24 h;
EXAMPLE 1 4′-[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazol-1-ylmethyl]biphenyl-2-carboxylic acid [0018] In a 2 litre reaction flask was added 400 ml methylene chloride, followed by 100 gm of 2-cyano-4′-methyl biphenyl. The reaction mass was stirred to get a clear solution and cooled to 20° C. Chlorine gas was sparged into the reaction mass for a period of 15 hours till completion of the reaction. The reaction was monitored by TLC using mobile phase n-hexane: ethyl acetate (8:2). The excess chlorine from the reaction mass was removed by flushing with nitrogen. The solvent was distilled out completely by distillation at atmospheric pressure and removal of the final traces under vacuum. To the residual mass, 500 ml of methyl isobutyl ketone was added. The reaction mass was stirred and washed with a solution of 300 ml of 5percent sodium bicarbonate solution. The lower aqueous layer was separated and the upper organic layer was washed with 300 ml water. The lower aqueous layer was separated. To the organic layer containing 4-chloromethyl-2′-cyanobiphenyl, the compound 2-n-propyl-4-methyl-6-(1′-methylbenzimidazol-2′-yl)benzimidazole was added, followed by a solution of 40 gm sodium hydroxide in 300 ml water. The reaction mass was stirred for 10 minutes and 10 gm of tetrabutyl ammonium hydrogen sulphate was added. The reaction mass was heated to 80° C. and maintained at 80 to 85° C. for 4 hours. [0019] The completion of the reaction was monitored by TLC using mobile phase chloroform: methanol (9:1). After completion of reaction, the lower aqueous layer was separated. The solvent was distilled out till mass temperature 120° C. and final traces were removed completely under vacuum. To the residual mass, 50 ml of n-butanol was added and the solvent distilled out under vacuum below 100° C. to remove all traces of methyl isobutyl ketone. The residue was dissolved in 750 ml of n-butanol and 83 gm sodium hydroxide added. The reaction mass was heated to reflux and maintained for 24 hours at 123 to 126° C. The completion of the reaction was monitored by TLC using mobile phase chloroform:methanol (9:1). [0020] The solvent was distilled out at atmospheric pressure till the mass temperature reached 140° C. The residual mass was cooled to 100° C. and 300 ml water was added. The solvent was distilled out azeotropically till the mass temperature reached 120° C. To the reaction mass 750 ml of water was added, the solution warmed to 80° C. The pH of the reaction mass was adjusted to 8.0 with hydrochloric acid. Finally the pH was adjusted to 6.0 with acetic acid, and the reaction mass maintained at 80 to 85° C. for one hour. The product obtained was filtered, washed with water and dried to yield 120 gm of 4′-[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazol-1-ylmethyl]biphenyl-2-carboxylic acid, which can be purified as per the procedure described mentioned in Example 5.
Reference: [1] Patent: US2015/197495, 2015, A1, . Location in patent: Paragraph 0018; 0019; 0020
[2] Patent: CN104768936, 2017, B, . Location in patent: Paragraph 0134-0135
  • 26
  • [ 114772-38-2 ]
  • [ 152628-02-9 ]
  • [ 144701-48-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With potassium hydroxide In dimethyl sulfoxide at 25 - 50℃; for 4 h;
Stage #2: With water; acetic acid In water; dimethyl sulfoxide at 20℃;
Example I Preparation of 14'-12-n-propvl-4-methvl-6-(1-methvl benzimidazol-2-yl) benzimidazol-1-yl methyl] biphenyl-2-carboxylic acidl 50 gm of [1H - Benzimidazole-2-n-propyl-4-methyl-6-(1'methyl benzimidazole-2'- yl) ] was added to 200 ml dimethyl sulfoxide and 50 gm of potassium hydroxide. To this was added 60 gm of methyl-4- (bromomethyl) at ambient temperature. The contents were stirred for 2 hours at 25-30 C, then heated to 40-50 C and maintained for 2 hours. About 500 ml water was added to the reaction mixture at room temperature and acidified to pH 4 with acetic acid. The reaction mixture was filtered and washed with purified water, dried under reduced pressure at 50-60 C to give 80 gm (88 percent) of the title product.
80%
Stage #1: With sodium hydroxide In dimethyl sulfoxide at 25 - 50℃; for 4 h;
Stage #2: With water; acetic acid In water; dimethyl sulfoxide
Example 3 Preparation of f4' - [2-n-propyl-4-methyl-6-(1-methyl benzimidazol-2-vl) benzimidazol -1-vl methvll biphenvl-2-carboxvlic acidl 50 gm of [1 H - Benzimidazole-2-n - propyl-4-methyl-6-(1'-methyl benzimidazole-2'- yl) ] was added to 200 ml dimethyl sulfoxide and 50 gm of sodium hydroxide. To this was added 60 gm of methyl-4- (bromomethyl) biphenyl-2-carboxylate at ambient temperature. The contents were stirred for 2 hours at 25-30 C and then heated to 40-50 and maintained for 2 hours. About 500 ml water was added to the reaction mixture and acidified with acetic acid to pH 4.2, extract4ed twice with 250 ml of dichloromethane and the combined extracts were concentrated and isolated by filtration after addition of 300 ml acetone, dried under reduced pressure at 50-60 C to give 75.0 gm (80percent) of the title compound.
Reference: [1] Patent: WO2005/108375, 2005, A1, . Location in patent: Page/Page column 2-4,7,9-10
[2] Patent: WO2005/108375, 2005, A1, . Location in patent: Page/Page column 2-4,8-10
  • 27
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  • [ 144701-48-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[2] Tetrahedron, 2012, vol. 68, # 11, p. 2509 - 2512
[3] Organic Process Research and Development, 2007, vol. 11, # 1, p. 81 - 85
[4] Patent: JP2016/53009, 2016, A,
[5] Patent: CN105130905, 2017, B,
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