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Chemical Structure| 139481-59-7
Chemical Structure| 139481-59-7
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Product Details of [ 139481-59-7 ]

CAS No. :139481-59-7 MDL No. :MFCD00864463
Formula : C24H20N6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :HTQMVQVXFRQIKW-UHFFFAOYSA-N
M.W : 440.45 Pubchem ID :2541
Synonyms :
CV 11974;Candesartan M1;Candesartan, CV11974, CV-1197, CV 11974, Trade names: Blopress, Atacand, Amias, and Ratacand

Safety of [ 139481-59-7 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:1325
Hazard Statements:H315-H319-H228 Packing Group:
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Application In Synthesis of [ 139481-59-7 ]

* 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.

  • Upstream synthesis route of [ 139481-59-7 ]
  • Downstream synthetic route of [ 139481-59-7 ]

[ 139481-59-7 ] Synthesis Path-Upstream   1~25

  • 1
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YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium hydroxide; water In methanol at 78 - 80℃; for 1 h;
Stage #2: With acetic acid In ethyl acetate at 10 - 15℃;
To the product obtained in Step A) (350 g) dissolved in methanol (1.17 L) was added sodium hydroxide solution (93 g in 1.17 L water). The reaction mass was heated to reflux at 78-80°C and maintained for 1 hour. After completion of reaction, methanol was completely removed under vacuum at 40-45°C and to the residue was added ethyl acetate (2. 8 L) and water (3.50 L) at room temperature. Stirred the mixture for about 1 hour at 25- 30°C and allowed to settle for 15 minutes. Separated the layers and pH of the aqueous layer was adjusted to 4-5 with acetic acid (about 450 g) at 10-15°C. The precipitated product was filtered and washed twice with water (2 x 0.7 L) and suck dried. The wet cake was air dried at room temperature for 2 hours and then at 50-55°C to afford the title compound. Yield: 323 g (95percent)
90% at 10 - 70℃; To 80.0 grams (0.176 moles) of methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl] benzimidazole-7-carboxylate, were added 265 ml ofmethanol, 535 ml of water, and 21.1 grams of sodium hydroxide, below 10°C, andthe mixture was heated to 70°C and maintained until the reaction completed. Themethanol was distilled off completely under reduced pressure, and the residuewas cooled to 10°C. The pH of the residue was adjusted to 2 with aqueoushydrochloric acid solution. The precipitated compound was filtered, washed withwater and dried at 60-70°C to get 70.0 grams (90percent) of 2-ethoxy-1-[[2'-(1 H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylicacid.
82% at 68 - 72℃; for 1 - 2 h; Industry scale An aqueous sodium hydroxide solution (73 kg/826L) was added to the wet MET (369.6 kg) obtained in Reference Example 9, and the mixture was stirred at 68 to 72 °C for 1 to 2 hours. The reaction solution was cooled, and washed twice with methylene chloride (486 kg) and once with toluene (366 L). Methanol (1437 L) was added to the aqueous layer, the pH was adjusted to 7.0 +/-0.5 with concentrated hydrochloric acid (about 35 L). Activated charcoal (11kg) was added, followed by stirring for about 30 minutes. The activated charcoal was filtered off, and concentrated hydrochloric acid (about 20L) was added until the solution became cloudy, followed by stirring at 25 +/-5°C for about 1 hour. Water (487 L) was added, and the pH was adjusted to 3.5 +/-0.3 with concentrated hydrochloric (about 85 L). After stirring at 24 to 30°C for about 30 minutes, water (687 L) was added, and the mixture was cooled to 10°C or lower, and stirred for about 1 hour. The crystals were separated, washed with water (412 L) and then acetone (427 L), ground, and dried to give 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid (200kg, 82.0percent). mp.183-185°C 1NMR (200MHz, DMSO-d6) δ: 1.38(3H,t), 4.58(2H,q), 5.63(2H,s), 6.97(4H.q), 7.17(1H,t), 7.47-7.68(6H,m) IR (KBr) cm-1:1710, 1550, 1480, 1430, 1280, 1240, 1040, 760
Reference: [1] Patent: WO2005/51929, 2005, A1, . Location in patent: Page/Page column 18
[2] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 17
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[4] Patent: EP1420016, 2004, A1, . Location in patent: Page 19
[5] Patent: US2009/203920, 2009, A1, . Location in patent: Page/Page column 4
[6] Patent: WO2009/157001, 2009, A2, . Location in patent: Page/Page column 4
[7] Patent: WO2011/145100, 2011, A1, . Location in patent: Page/Page column 7
[8] Patent: US2018/155326, 2018, A1, . Location in patent: Paragraph 0035
  • 2
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YieldReaction ConditionsOperation in experiment
85% With lithium hydroxide In ethanol at 80℃; for 3 h; A solution of ethyl 2-ethoxy-1-[{2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]-1,1'-biphenyl-4-yl}methyl]-benzimidazole-7-carboxylate (0.28g) and 1M LiOH (1.2 ml) in ethanol (3.5 ml) was stirred at 80°C for three hours. The reaction mixture was concentrated and washed with toluene (5x2ml). The aqueous layer was adjusted to pH 2-3 with 1 M HCl to give a white solid (0.15g, 85percent yield) corresponding to 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-benzimidazole-7-carboxylic acid. 1H-NMR (400MHz, DMSO) δ 1.37 (t, J=7Hz, 3H), 4.57 (q, J=7Hz, 2H), 5.62 (s, 2H), 6.95 (q, 4H), 7.17 (t, J=8Hz, 1H), 7.46 (m, 1 H), 7.5 (m, 2H), 7.6-7.7 (m, 3H) ppm.
Reference: [1] Patent: EP1833801, 2008, B1, . Location in patent: Page/Page column 17; 18
  • 3
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YieldReaction ConditionsOperation in experiment
80%
Stage #1: for 24 h; Heating / reflux
Stage #2: With hydrogenchloride In ethanol; water
Example 14.
Obtaining candesartan I
I 3.5 ml of a 2M soda solution is added to a solution of 0.24 g of ethyl 2-ethoxy-l- (2H-tetrazole-5-yl) [1, 1 '- biphenyl] -4-yl] methyl] -lH-benzimidazole-7-carboxylate in 4 ml of ethanol and is heated at reflux for 24 hours. The crude reaction product is adjusted to pH 4-4.5 with concentrated HCl. A solid is precipitated in the reaction medium and then filtered, washed with water and dried in a vacuum oven at 40°C, to obtain 0.18 g (80percent) of dry product .
Reference: [1] Patent: WO2006/134078, 2006, A1, . Location in patent: Page/Page column 21
[2] Patent: WO2008/44244, 2008, A2, . Location in patent: Page/Page column 5
[3] Patent: US2018/155326, 2018, A1, . Location in patent: Paragraph 0031-0034
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YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide In ethanol WORKING EXAMPLE 5
2-Ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-benzimidazole-7-carboxylic acid
A solution of ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylate (0.24 g) and 1N NaOH (1.5 ml) in ethanol (4 ml) was stirred at 80° C. for one hour.
The reaction mixture was concentrated, and the concentrate was extracted with water and ethyl acetate.
The aqueous layer was adjusted to pH 3-4 with 1N-HCl to give crystals.
Recrystallization of the crystals from ethyl acetate-methanol afforded colorless crystals (0.15 g, 67percent), m.p. 183°-185° C.
1 H-NMR(200 MHz,DMSO-d6) δ: 1.38(3H,t), 4.58(2H,q), 5.63(2H,s), 6.97(4H,q), 7.17(1H,t), 7.47-7.68(6H,m)
IR(KBr) cm-1: 1710, 1550, 1480, 1430, 1280, 1240, 1040, 760
Reference: [1] Patent: US5196444, 1993, A,
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Reference: [1] Drug Metabolism and Disposition, 2013, vol. 41, # 11, p. 1888 - 1895
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2011/145100, 2011, A1,
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2011/145100, 2011, A1,
  • 8
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2011/145100, 2011, A1,
  • 9
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2011/145100, 2011, A1,
  • 10
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2011/145100, 2011, A1,
  • 11
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2011/145100, 2011, A1,
  • 12
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: US2018/155326, 2018, A1,
  • 13
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 14
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 15
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Reference: [1] Patent: WO2006/134078, 2006, A1,
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Reference: [1] Patent: WO2006/134078, 2006, A1,
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Reference: [1] Patent: WO2006/134078, 2006, A1,
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Reference: [1] Patent: WO2006/134078, 2006, A1,
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Reference: [1] Patent: WO2006/134078, 2006, A1,
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Reference: [1] Patent: WO2006/134078, 2006, A1,
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Reference: [1] Patent: CN107056757, 2017, A,
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Reference: [1] Patent: US2018/155326, 2018, A1,
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YieldReaction ConditionsOperation in experiment
94% With triethylamine In dichloromethane at 15 - 23℃; for 3.5 h; Flow reactor; Large scale I. Candesartan (10kg) and methylene chloride (100kg) were added to the reactor, and the temperature was lowered to 15°C. Triethylamine (4.5kg) was slowly added dropwise; after the addition was completed, the temperature of the reaction system was raised to 23°C. Triphenylchloromethane (7kg) was added in portions; after the addition, the reaction system temperature was maintained at 23°C for 3.5 hours; TLC monitoring (developer dichloromethane:methanol = 10:1 (V/V),Rf = 0.78) After the reaction is complete, add 0.1 mol/L HCl 30L (system pH = 5.4) at a time, add 5L 9mol/L HCl slowly to pH = 2.2, and separate the aqueous and organic layers by standing. 60L for the organic layer. The saturated saline solution was washed, transferred to a vacuum vessel, and the dichloromethane was recovered under reduced pressure.The residue in the kettle was added with 65 L of ethanol, and the temperature was raised to 45° C. and stirred for 3 hours until a large amount of white solid precipitated. The heating was stopped, and the temperature was lowered to room temperature. The filter cake was washed with a small amount of ethanol and dried at normal pressure at 50° C. for 12 hours to obtain three. Phenyl candesartan (white crystalline powder, 14.5 kg). Calculated according to the following formula, the yield of this step is 94.0percent.
90% With triethylamine In acetone at 55 - 60℃; for 4 - 8 h; Examples-l; Preparation of tritylated Candesartan acid (acetone) A mixture of Candesartan acid, triethylamine and acetone was heated to reflux temperature at 55-600C. To this trityl chloride solution in acetone was added and refluxed it for 4-8 hours. The reaction mixture was cooled at ambient temperature followed by addition of D. M. water and stirred for one hour. The reaction mixture was filtered and washed with mixture of acetone and D. M. water. To the solid, D. M water was added and stirred for 30 minutes at ambient temperature. The mixture was filtered and washed with D. M. water. The solid was dried to obtain tritylated Candesartan acid. Yield: 90 percent Purity: 99percent
90% With triethylamine In acetone at 55 - 60℃; A mixture of Candesartan acid, triethylamine and acetone was heated to reflux temperature at 55-60° C. To this trityl chloride solution in acetone was added and refluxed it for 4-8 hours. The reaction mixture was cooled at ambient temperature followed by addition of D. M. water and stirred for one hour. The reaction mixture was filtered and washed with mixture of acetone and D. M. water. To the solid, D. M water was added and stirred for 30 minutes at ambient temperature. The mixture was filtered and washed with D. M. water. The solid was dried to obtain tritylated Candesartan acid.Yield: 90percentPurity: 99percent
89% With triethylamine In methyl iso-butyl ketone (MIBK) at 55 - 60℃; for 4 - 8 h; ExampIes-2; Preparation of tritylated Candesartan acid (MIBK)A mixture of Candesartan acid, triethylamine and methyl isobutyl ketone (MIBK) was heated to reflux temperature at 55-600C. To this trityl chloride solution in MIBK was added and refluxed it for 4-8 hours. The reaction mixture was cooled at ambient temperature followed by addition of D. M. water and stirred for one hour. The reaction mixture was filtered and washed with mixture of acetone and D. M. water. To the solid, D. M water was added and stirred for 30 minutes at ambient temperature. The mixture was filtered and washed with D. M. water. The solid was dried to obtain tritylated Candesartan acid. Yield: 89 percent Purity: 98.5percent
88% With triethylamine In butanone at 55 - 60℃; for 4 - 8 h; Examples-3; Preparation of tritylated Candesartan acid (MEK) A mixture of Candesartan acid, triethylamine and methyl ethyl ketone (MEK) was heated to reflux temperature at 55-600C. To this trityl chloride solution in MEK was added and refluxed it for 4-8 hours. The reaction mixture was cooled at ambient temperature followed by addition of D. M. water and stirred for one hour. The reaction mixture was filtered and washed with mixture of acetone and D. M. water. To the solid, D. M water was added and stirred for 30 minutes at ambient temperature. The mixture was filtered and washed with D. M. water. The solid was dried to obtain tritylated Candesartan acid. Yield: 88 percent .bul. Purity: 98percent
83.8% With triethylamine In dichloromethane at 25 - 30℃; for 2 h; Heating / reflux Example-1: Preparation of Candesartan cilexetil (with isolation of cilexetil trityl candesartan); Step-I: Preparation of Trityl candesartanTo solution of Candesartan (10Og in 350 ml MDC) and triethyl amine (34.3 g) Trityl chloride (76.8g in 150 ml MDC) is added slowly at temperature of 25 - 3O0C. Temperature of the reaction mass is raised and maintained at reflux temperature for 2 hrs. Reaction mass is cooled to temperature of 30 - 350C, water (100 ml) is added, stirred for about 15 min, allowed to settle and separated the layers. Aqueous layer is extracted with MDC (2x 100 ml), combined organic layer is washed with water and MDC is removed below 5O0C from organic layer. Ethyl acetate (600 ml) is added, raised and maintained the temperature of the reaction mass at reflux temperature for 2hrs. The temperature of the mass is cooled, maintained for 1 hr at 25 - 3O0C and isolated the product by filtration. Wet cake is washed with ethyl acetate (100 ml) and dried at temperature of 45 - 5O0C to constant weight. <n="7"/>The weight of trityl candesartan is 130 g (Yield 83.8percent)
53% With triethylamine In dichloromethane at 20℃; for 2.5 h; To a solution of 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-benzimidazole-7-carboxylic acid (78 mg) in methylene chloride (1ml) were added trityl chloride (63 mg) and triethylamine (0.03ml). The mixture was stirred at room temperature for two hours thirty minutes. The reaction mixture was washed with water, dried and concentrated to dryness. The residue was purified by column chromatography on silica (eluant: cyclohexane /ethyl acetate: from to 90/10 to 0/100) to give 2-ethoxy-1-[{2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]-1,1'-biphenyl-4-yl}methyl]-benzimidazole-7-carboxylic acid (60mg, 53percent yield) as a white solid. 1H-NMR (400MHz, CDCl3) δ 1.40 (t, J=7Hz, 3H), 4.62 (q, J=7Hz, 2H), 5.59 (s, 2H), 6.76 (d, J=8Hz, 2H), 6.92-6.96 (m, 8H), 7.14 (t, J=8Hz, 1 H), 7.19-7.30 (m, 10H), 7.38 (m, 2H), 7.64 (d, J=8Hz, 1 H), 7.76-7.83 (m, 2H) ppm.
125.5 g With triethylamine In dichloromethane at 25 - 35℃; for 20 h; 250 g of tributyl tin azide was added into 600 ml of xylene. 100 g of candesartan cyclic compound (in formula II, R is ethyl) was added, heated to 140-150° C., and refluxed to react for 20 h. After the end of the reaction, the reaction mixture was cooled to 40-50° C. 600 ml of sodium hydroxide solution (48 g of sodium hydroxide dissolved in 600 ml of water) was added, and stirred under 20-35° C. (0032) The organic layer was removed. (0033) The alkaline aqueous layer was heated to 70-80° C. to completely hydrolyze candesartan ethyl ester. The temperature of the mixture was controlled at 25-35° C. 400 ml of dichloromethane was added. Glacial acetic acid was added dropwise to adjust pH of the mixture to 5-6 to precipitate candesartan. (0034) Triethylamine was added dropwise into the mixture until the candesartan solid was dissolved completely. The dichloromethane layer was separated. The aqueous layer was extracted by adding 200 ml of dichloromethane once again. The organic layers were combined. 68 g of triphenyl chloromethane was added into the organic layer. The temperature of the mixture was controlled at 25-35° C. to react until the content of candesartan was reduced to less than 1.0percent monitored by HPLC. After the end of the reaction, 100 ml of water was added for washing. The aqueous layer was removed. The organic layer was dried under reduced pressure. 600 ml of anhydrous ethanol was added to crystallize. The resulting crystals were collected by filtration, and dried to provide 125.5 g of trityl candesartan, yield 78.2percent, purity 97

Reference: [1] Patent: CN105153124, 2018, B, . Location in patent: Paragraph 0005; 0054; 0055; 0076; 0090
[2] Patent: WO2009/7986, 2009, A1, . Location in patent: Page/Page column 13
[3] Patent: US2010/210852, 2010, A1, . Location in patent: Page/Page column 5
[4] Patent: WO2009/7986, 2009, A1, . Location in patent: Page/Page column 14
[5] Patent: WO2009/7986, 2009, A1, . Location in patent: Page/Page column 14
[6] Patent: WO2007/94015, 2007, A1, . Location in patent: Page/Page column 5-6
[7] Patent: EP1833801, 2008, B1, . Location in patent: Page/Page column 18
[8] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 23, p. 7971 - 7977
[9] Patent: WO2006/50922, 2006, A1, . Location in patent: Page/Page column 12
[10] Patent: WO2009/157001, 2009, A2, . Location in patent: Page/Page column 4
[11] Patent: WO2011/92666, 2011, A1, . Location in patent: Page/Page column 12
[12] Patent: WO2011/145100, 2011, A1, . Location in patent: Page/Page column 7-8
[13] Patent: US2018/155326, 2018, A1, . Location in patent: Paragraph 0031-0034
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YieldReaction ConditionsOperation in experiment
66% With triethylamine In dichloromethane WORKING EXAMPLE 6
2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid
To a solution of 2-ethoxy-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid (2.07 g) in methylene chloride (10 ml) were added trityl chloride (1.59 g) and triethylamine (0.8 ml).
The mixture was stirred at room temperature for one hour.
The reaction mixture was washed with water, dried and concentrated to dryness.
The residue was purified by column chromatography on silica gel to give crystals.
Recrystallization of crude crystals thus obtained from ethyl acetate-benzene gave colorless crystals (2.12 g, 66percent), m.p. 168°-170° C.
1 H-NMR(200 MHz, CDCl3) δ: 1.40(3H,t), 4.61(2H,q), 5.58(2H,s), 6.76(2H,d), 6.91-6.96(8H,m), 7.12(1H,t), 7.17-7.41(12H,m), 7.60(1H,dd), 7.73-7.82(2H,m)
Reference: [1] Patent: US5196444, 1993, A,
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Reference: [1] Patent: US6177587, 2001, B1,
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