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Chemical Structure| 139481-44-0
Chemical Structure| 139481-44-0
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Product Details of [ 139481-44-0 ]

CAS No. :139481-44-0 MDL No. :MFCD09031384
Formula : C25H21N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :KSXLHOFDCDKQLH-UHFFFAOYSA-N
M.W : 411.45 Pubchem ID :15654674
Synonyms :

Calculated chemistry of [ 139481-44-0 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 21
Fraction Csp3 : 0.16
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 118.21
TPSA : 77.14 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.89
Log Po/w (XLOGP3) : 4.9
Log Po/w (WLOGP) : 4.81
Log Po/w (MLOGP) : 3.34
Log Po/w (SILICOS-IT) : 4.83
Consensus Log Po/w : 4.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.52
Solubility : 0.00125 mg/ml ; 0.00000304 mol/l
Class : Moderately soluble
Log S (Ali) : -6.26
Solubility : 0.000228 mg/ml ; 0.000000555 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.13
Solubility : 0.00000304 mg/ml ; 0.0000000074 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.28

Safety of [ 139481-44-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 139481-44-0 ]

* 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 [ 139481-44-0 ]
  • Downstream synthetic route of [ 139481-44-0 ]

[ 139481-44-0 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 78-09-1 ]
  • [ 136304-78-4 ]
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YieldReaction ConditionsOperation in experiment
84.8% at 78 - 82℃; for 1 - 2 h; Heating / reflux; Industry scale The concentrate of methyl 3-amino-2-N-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate [MBA] obtained in Reference Example5, tetraethyl orthocarbonate [TEC] obtained in Reference Example 6 (397 kg) and acetic acid (62 kg) were mixed, and the mixture was heated (78 to 82°C) under reflux for about 1 to 2 hrs..
The reaction solution was cooled, and methanol (1680 L), a 24percent aqueous sodium hydroxide solution (65 L) and water (2030 L) were added..
The mixture was stirred at 60 to 30°C for 2 hours, and the PH was adjusted to 5 to 7..
After cooled to 5°C or lower, the precipitated crystals were separated, and washed with cold water (2500 L) and cold ethyl acetate (500 L) to give first crystals..
The mother liquor and the washing were concentrated under reduced pressure, followed by cooling to 5°C or lower, and the precipitated crystals were separated, and washed with cold ethyl acetate (20 L) to give second crystals..
The first and second crystals were combined, and dissolved in ethyl acetate (4890 L) under reflux..
A seed crystal was added at about 70°C, and cooled to 5 °C.
The crystals were separated, and washed with cold ethyl acetate (200 L), followed by drying to give methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate [BEC](361 kg, 84.8percent). mp. 168.5-169.5°C 1H-NMR(200MHz, CDCl3) δ: 1.42(3H,t), 3.71(3H,s), 4.63(2H,q), 5.59(2H,s), 7.09(2H,d), 7.20(1H,t), 7.45-7.59(5H,m), 7.69-7.80(2H,m), 7.92(1H,dd) IR(KBr) cm-1: 2225, 1725, 1550, 1480, 1430, 1280, 1250, 1040, 760, 750
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: EP1420016, 2004, A1, . Location in patent: Page 18-19
[3] Patent: WO2009/157001, 2009, A2, . Location in patent: Page/Page column 3
  • 2
  • [ 150058-27-8 ]
  • [ 114772-54-2 ]
  • [ 139481-44-0 ]
Reference: [1] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 16; 21-22
[2] Patent: CN107089972, 2017, A, . Location in patent: Paragraph 0032; 0035; 0037
  • 3
  • [ 21606-04-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 4
  • [ 73833-13-3 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 5
  • [ 603-11-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 6
  • [ 57113-90-3 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 7
  • [ 856414-36-3 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 8
  • [ 139481-38-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 9
  • [ 139481-28-0 ]
  • [ 139481-44-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
  • 10
  • [ 139481-44-0 ]
  • [ 139481-69-9 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With sodium azide; tributyltin chloride In toluene at 110 - 115℃; for 24 h; Heating / reflux
Stage #2: With acetic acid In methanol; water; toluene at 15 - 20℃; for 1 h;
Preparation of 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- lH-benzimidazole-7-carboxylic acid methyl ester To 2-ethoxy-1-[[2'-cyano [l, 1'-biphenyl] -4-yl] methyl]-lH-benzimidazole-7- carboxylic acid methyl ester of Formula IV (310 g) in toluene (2.48 L) added tributyltin chloride (737 g) and sodium azide (146 g) and tetrabutyl ammonium bromide (31 g). The resultant mass was slowly heated to 110°C and maintained for 24 hours at 110-115°C. The reaction was monitored by TLC and after completion of reaction, the reaction mass was cooled to 15°C. Added methanol (3.1 L) and water (2.17 L) to the reaction mass followed by addition of acetic acid (930 g). The resultant mixture was stirred at 15-20°C for 1 hour to allow separation of the product. Charged toluene (1.24 L) at 15-20°C and filtered the reaction mass. Washed the cake thoroughly with water (0.93 L) to completely remove the acidity (until the pH of the washing is between about 5.5 to about 7.0). Washed the cake with toluene (0.62 L) and suck dried. Air dried the product at 50-55°C to afford the title compound. Yield: 290 g (85percent)
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: WO2005/51929, 2005, A1, . Location in patent: Page/Page column 18
[3] Patent: US2009/203920, 2009, A1, . Location in patent: Page/Page column 4
[4] Patent: EP1420016, 2004, A1, . Location in patent: Page 19
[5] Patent: WO2009/157001, 2009, A2, . Location in patent: Page/Page column 3
[6] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 16-17
[7] Patent: US2018/155326, 2018, A1, . Location in patent: Paragraph 0035
  • 11
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  • [ 139481-69-9 ]
YieldReaction ConditionsOperation in experiment
100% With sodium nitrite In ethanol; hexane; ethyl acetate; toluene EXAMPLE 5
Methyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate
A mixture of 13.0 g of methyl 1-(2'-cyanobiphenyl-4-yl)methyl-2-ethoxybenzimidazole-7-carboxylate, 47.1 g of trioctyltin azide (tri-n-octyltin azide) and 60 ml of toluene was refluxed at 125° C. for 31 hours.
After cooling, the reaction mixture was concentrated.
To the concentrate was added 56 ml of ethanol as well as an aqueous solution of sodium nitrite (7.7 g/28 ml) and the mixture was adjusted to pH 5 with concentrated hydrochloric acid.
Then, 31 ml of ethyl acetate was added.
The mixture was further adjusted to pH 1.1 with concentrated hydrochloric acid, diluted with 20 ml of n-hexane and adjusted to pH 3.3 with 1N aqueous sodium hydroxide solution.
The crystals were separated, washed with ethyl acetate/n-hexane mixture (1:3) and dried to provide 14.56 g of methyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7carboxylate.
Yield 100percent. 1 H NMR (CDCl3) δ: 1.42 (3H, t), 3.56 (3H, s), 4.27 (2H, q), 5.54 (2H, s), 6.70 (2H, d), 6.78-6.95 (4H, m), 7.28-7.33 (1H, m), 7.40 (1H, dd), 7.56-7.66 (2H, m), 8.02-8.06 (1H, m)
IR(KBr): 1720, 1618, 1548, 1476, 1432, 1390, 1354, 1324, 1284, 1222, 1134, 1042, 872, 840, 820, 780, 756 cm-1.
Reference: [1] Patent: US5484955, 1996, A,
  • 12
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  • [ 139481-59-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: US2018/155326, 2018, A1,
  • 13
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  • [ 147403-65-4 ]
YieldReaction ConditionsOperation in experiment
90% With hydroxylamine hydrochloride; sodium hydrogencarbonate In N,N-dimethyl acetamide; water at 70℃; for 18 h; N, N-dimethylacetamide 2L,Water 16L, added to the reaction bottle,Hydroxylamine hydrochloride (3.37 kg 48.6 mol) was added,Sodium carbonate (5.15 kg 48.6 mol) was added,1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylic acid methyl ester(2 kg, 4.86 mol)70 ° C for 18 hours,Cooling, adding water 2L,Precipitation of solid,Filtration was 2-ethoxy-1-[2'-(N'-hydroxycarbamimidoyl)biphenyl-4-yl]-1H-benzimidazole-7-carboxylic acid methyl ester (1.94 g, 37.70 mol),Reference is made to Examples1HPLC conditions Purity: 98.9percent Yield: 90percent.
85% With hydroxylamine hydrochloride; sodium hydrogencarbonate In dimethyl sulfoxide at 80 - 85℃; for 20 h; Dimethyl sulfoxide (75 mL) and hydroxylamine hydrochloride (6 g) were stirred at 20°C to 30°C. Sodium bicarbonate (9 g) was added to the solution and stirred at 45 °C to 50 °C for 1 hour. Methyl-1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (3 g) was added to the reaction mixture and heated at 80 °C to 85 °C for 20 hours. The reaction mixture was cooled to 20 °C to 30 °C and de-ionized water (75 mL) was added to the reaction mixture. The solid obtained was filtered and washed with water (75 mL). The solid obtained was purified in 2-butanol (15 mL) at 90 °C to 95 °C for 4 hours and further cooled to 20 °C to 30 °C for 4 hours. The solid obtained was filtered, washed with 2-butanol (6 mL), and dried to obtain the title compound. Yield: 2.75 g (85percent) HPLC Purity: 96.89percent
70.4% With hydroxylamine hydrochloride; sodium carbonate In dimethyl sulfoxide at 90℃; To a 500 mL four-neck flask, 20 g of Compound 1 was added, and while stirring, 100 mL of dimethyl sulfoxide solution in which 10.14 g (3 eq) of hydroxylamine hydrochloride was added was added, and the mixture was heated to 90 DEG C and 30.95 g (6 eq) was added in portions under stirring. Sodium carbonate, after the completion of the reaction for 9-10 hours, after the completion of the reaction, it is allowed to come to room temperature, and 100 mL of water is added to stir the mixture. The solid precipitates, which is cooled down to 0-5°C. Stirring is continued for about 1 hour, and the mixture is dried by suction to obtain 15.2 g of compound 2. The yield was 70.4percent.
55 g With hydroxylamine hydrochloride; sodium hydroxide In methanol; N,N-dimethyl acetamide at 10 - 75℃; for 0.5 h; Inert atmosphere Methanol (400 mL) and sodium hydroxide (56.44 g) were added under a nitrogen atmosphere and stirred at 20° C. to 30° C. to get a clear solution. Dimethylacetamide (750 mL) and hydroxylamine hydrochloride (101.45 g) were added under a nitrogen atmosphere and stirred at 20° C. to 30° C. to get clear solution. Methanolic sodium hydroxide solution was added to the solution of hydroxylamine hydrochloride in dimethylacetamide at 25° C. to 30° C. The reaction mixture was stirred for 30 minutes. Methyl-1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (100 g) was added to the reaction mixture at 25° C. to 30° C. and heated to 70° C. to 75° C. for 16 hours to 20 hours. The reaction mixture was cooled to 10° C. to 15° C. The reaction mixture was added to deionized water (1000 mL) at 10° C. to 25° C. The pH of the reaction mixture was adjusted to 0.8 to 1.2 using concentrated hydrochloric acid (150 mL). The reaction mixture was stirred for 30 minutes at 20° C. to 30° C. The reaction mixture was filtered through celite and washed with deionized water (100 mL). The aqueous layer was washed with toluene (500 mL) at 25° C. to 30° C. and the pH of the aqueous layer was adjusted to 8.8 to 9.2 using 30percent solution of sodium carbonate (500 mL) at 20° C. to 30° C. The reaction mixture was stirred for 3 hours to 4 hours at 25° C. to 30° C. The reaction mixture was filtered and washed with deionized water (100 mL) at 20° C. to 30° C. Isobutanol (500 mL) was added to the reaction mixture at 20° C. to 30° C. and the reaction mixture was heated to 90° C. to 95° C. The reaction mixture was stirred for 2 hours at 90° C. to 95° C., cooled to 25° C. to 30° C., and stirred for 4 to 6 hours at 25° C. to 30° C. The reaction mixture was filtered and washed with isobutanol (100 mL) at 20° C. to 30° C. The reaction mixture was dried under vacuum for 30 minutes at 20° C. to 30° C. and then at 45° C. to 50° C. to obtain the title compound. Yield: 55 g
191.3g With hydroxylamine hydrochloride; sodium hydrogencarbonate; sodium sulfite In dimethyl sulfoxide at 50 - 85℃; for 12 h; Taking anhydrous sodium sulfite 122.5 g (0.972 mol)Sodium bicarbonate 408.4 g (4.861 mol)Was added to 2.4 L of DMSO, stirred,A mixture of hydroxylamine hydrochloride (270.2 g, 3.889 mol)Temperature control 50 ~ 55 stirring reaction 2h,Was added 1 - [(2 - cyanobiphenyl-4-yl) methyl] -2-ethoxy-benzimidazole-7-carboxylate (200g, 0.486mol),Temperature control 80 ~ 85 stirring reaction 10h,Rapid dropwise addition of 2.4L water stirring crystallization,Temperature control 20 ~ 25 stirring for 1h,Filtration to give compound II191.3g.HPLC was used to detect compound II 99.07percent and amide impurity 0.32percent.

Reference: [1] Patent: CN103408500, 2016, B, . Location in patent: Paragraph 0026; 0046-0047
[2] Patent: WO2013/114305, 2013, A1, . Location in patent: Page/Page column 15; 16
[3] Organic Process Research and Development, 2015, vol. 19, # 4, p. 514 - 519
[4] Organic Process Research and Development, 2013, vol. 17, # 1, p. 77 - 86
[5] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 4, p. 929 - 936
[6] Patent: CN103242305, 2018, B, . Location in patent: Paragraph 0038-0040
[7] Journal of Medicinal Chemistry, 1996, vol. 39, # 26, p. 5228 - 5235
[8] Patent: WO2012/107814, 2012, A1, . Location in patent: Page/Page column 13
[9] Patent: US2015/11774, 2015, A1, . Location in patent: Paragraph 0052; 0053
[10] Patent: CN106478515, 2017, A, . Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0038
[11] Patent: CN108456202, 2018, A, . Location in patent: Paragraph 0026; 0028; 0030; 0032; 0034; 0036-0038; 0042
  • 14
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  • [ 147404-76-0 ]
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YieldReaction ConditionsOperation in experiment
71.7% With hydroxylamine; triethylamine In ethanol; water for 20 h; Reflux methyl 1-[(2’-cyanobiphenyl-4-yl)methyl] -2-ethoxybenzimidazole-7-carboxylate (0.4 g, 0.97 mmol), 50percent aqueous hydroxylamine solution (1.0 g, 14.5 mmol), Triethylamine (0.1 g, 0.97 mmol) in ethanol (10 ml) was refluxed for 20 h, cooled to crystallize, and filtered to give the title compound (0.31 g, yield 71.7percent).The liquid phase data of the reaction liquid after 20 h showed that the amide impurity: product (liquid chromatographic area ratio): raw material = 7.17: 78.2: 0.
63% With hydroxylamine; triethylamine In ethanol; water for 24 h; Raw material (compound 2A) 20 g, in the reaction bottle, adding ethanol to 200 ml, triethylamine 5 g, 50percent aqueous hydroxylamine solution 37 g, reaction 24h, the cooling crystallization, the white solid obtained 13.6 g (63.0percent). HPLC detection reaction in the reaction solution at the end of the major amide impurity (compound 6A): product is 7.15percent : 92.84percent (that is, the impurity and the product of the ratio of 1 : 12.9), see Figure 2.
Reference: [1] Patent: CN102344415, 2016, B, . Location in patent: Paragraph 0021-0022
[2] Patent: CN103664792, 2016, B, . Location in patent: Paragraph 0097-0099
[3] Patent: CN103664920, 2016, B, . Location in patent: Paragraph 0097; 0098; 0099
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Reference: [1] Patent: WO2012/119573, 2012, A1, . Location in patent: Page/Page column 12-13
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Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 4, p. 514 - 519
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Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 4, p. 514 - 519
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  • [ 139481-72-4 ]
Reference: [1] Patent: US2018/155326, 2018, A1,
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Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

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Chemical Structure| 150058-27-8

[ 150058-27-8 ]

Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

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Chemical Structure| 147403-52-9

[ 147403-52-9 ]

Methyl 2-ethoxy-1-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

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Chemical Structure| 1403474-70-3

[ 1403474-70-3 ]

Ethyl 2-ethoxy-1-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Similarity: 0.71