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Chemical Structure| 14719-83-6
Chemical Structure| 14719-83-6
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Product Details of [ 14719-83-6 ]

CAS No. :14719-83-6 MDL No. :MFCD00016989
Formula : C8H6ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :XRTKWPWDSUNLHS-UHFFFAOYSA-N
M.W : 215.59 Pubchem ID :735797
Synonyms :

Calculated chemistry of [ 14719-83-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.55
TPSA : 72.12 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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 2.31
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 0.22
Consensus Log Po/w : 1.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.382 mg/ml ; 0.00177 mol/l
Class : Soluble
Log S (Ali) : -3.46
Solubility : 0.0743 mg/ml ; 0.000345 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.717 mg/ml ; 0.00333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 14719-83-6 ]

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 [ 14719-83-6 ]

* 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 [ 14719-83-6 ]
  • Downstream synthetic route of [ 14719-83-6 ]

[ 14719-83-6 ] Synthesis Path-Upstream   1~22

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  • [ 1670-82-2 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 15, p. 1653 - 1656
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  • [ 68867-17-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
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  • [ 26000-33-9 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 13, p. 5014 - 5019
[2] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 154 - 165
  • 4
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  • [ 14192-26-8 ]
Reference: [1] Patent: , 2016, ,
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  • [ 23616-15-1 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4998 - 4999
  • 6
  • [ 67-56-1 ]
  • [ 96-99-1 ]
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YieldReaction ConditionsOperation in experiment
92% at 0℃; for 6 h; Heating / reflux Methyl 4-chloro-3-nitrenzoate (1). Dissolve 4-chloro-3-nitro-benzoic acid (5.0 g, 24.8 mmol) in 200 ml of methanol and add 4.15 ml (29.8 mmol) of triethylamine. Cool in an ice-salt bath and add drop by drop 3.19 ml (44.7 mmol) of acetyl chloride. Agitate at reflux for 6 hours. Evaporate the solvent under reduced pressure. Take up the residue with 100 ml of water and extract 2 times with ethyl acetate (100 ml). Dry the organic phase on MgSO4 and vaporize it under reduced pressure and purify it with ether (10 ml) (4.81 g, 92percent). Rf=0.55 (EtOAc/Cyclohexane=7/3); mp 79-80° C.; ir CO 1716 cm-1; 1H-NMR(300 MHz, DMSO-d6) δ 3.90 (s, 3H, OCH3), 7.90 (d, 1H, H5, J5-6=8.1 Hz), 8.15 (dd, 1H, H6, J6-5=8.1 Hz, J5-2=1.5 Hz), 8.49(d, 1H, H2, J2-6=1.5 Hz). Anal. (C8H6ClNO4).
88.8% for 3.25 h; Heating / reflux Synthesis of the 6-methoxycarbonyl-2-oxindole in accordance with the process shown in synthesis scheme C.Synthesis of benzoic acid, 4-chloro-3-nitro-, methylester20kg of 4-chloro-3-nitro-benzoic acid ( 99,22mol) is suspended in 76L methanol. 5,9kg thionylchloride (49,62mol) is added within 15 minutes and refluxed for about 3 hours. After cooling to about 5°C, the product is isolated by centrifugation and drying at 45°C. Yield: 19,0kg (88,8percent of theoretical amount) <n="16"/>Purity (HPLC): 99,8percent
88.8% for 3 h; Heating / reflux Example 1 : Synthesis of the 6-methoxycarbonyl-2-oxindole in accordance with the process shown in synthesis scheme C.; Synthesis of benzoic acid, 4-chloro-3-nitro-, methylester; 20kg of 4-chloro-3-nitro-benzoic acid ( 99,22mol) is suspended in 76L methanol. 5,9kg thionylchloride (49,62mol) is added within 15 minutes and refluxed for about 3 hours. After cooling to about 5°C, the product is isolated by centrifugation and drying at 45°C. Yield: 19,0kg (88,8percent of theoretical amount) Purity (HPLC): 99,8percent
88.5% at 70℃; for 3 h; After 200g (1mol) 4-chloro-3-nitrobenzoic acid was suspended in methanol, Within 15 min, add 59g (490mmol) thionyl chloride. Heat at reflux. After reacting at 70 °C for 3 hours, cool to 5 °C, products pass through the centrifugal separation, the 45 °C drying, to obtain the solid 189.2g, the target compound, the yield is 88.5percent.
83% at 0℃; for 17 h; Reflux 4-Chloro-3-nitro benzoic acid (40.0g, 0.02mol) was suspended in methanol (200mL) and cooled down to 0°C. Concentrated sulfuric acid (22mL) was slowly added with stirring, and then the mixture was heated at reflux for 17h. Upon cooling to room temperature, a precipitate formed, which was collected by filtration and washed with cold methanol (2×30mL) and hexane (2×30mL) to afford the methyl ester as a white solid (35.5g, 83percent).

Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3927 - 3936
[2] Heterocyclic Communications, 2001, vol. 7, # 5, p. 455 - 460
[3] Chemical Research in Toxicology, 1997, vol. 10, # 4, p. 439 - 449
[4] Synthetic Communications, 2002, vol. 32, # 11, p. 1703 - 1707
[5] Journal of Organic Chemistry, 2003, vol. 68, # 14, p. 5525 - 5533
[6] Patent: US2007/54899, 2007, A1, . Location in patent: Page/Page column 9
[7] Asian Journal of Chemistry, 2011, vol. 23, # 5, p. 2007 - 2010
[8] Patent: WO2009/71524, 2009, A2, . Location in patent: Page/Page column 14-15; 5
[9] Patent: WO2009/71523, 2009, A1, . Location in patent: Page/Page column 6; 16
[10] Patent: , 2016, , . Location in patent: Paragraph 0046; 0064; 0065
[11] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 427 - 438
[12] Journal of the American Chemical Society, 1962, vol. 84, p. 837 - 847
[13] Canadian Journal of Chemistry, 1971, vol. 49, p. 583 - 587
[14] Synthetic Communications, 2002, vol. 32, # 11, p. 1647 - 1652
[15] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1587 - 1597
[16] Archiv der Pharmazie, 2007, vol. 340, # 11, p. 607 - 611
[17] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731
[18] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 4, p. 1036 - 1041
[19] Asian Journal of Chemistry, 2011, vol. 23, # 12, p. 5471 - 5476
[20] Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2573 - 2578
[21] Journal of the American Chemical Society, 2014, vol. 136, # 12, p. 4551 - 4556
[22] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7310 - 7327
[23] Patent: WO2017/143011, 2017, A1, . Location in patent: Paragraph 0664-0666
[24] Letters in Drug Design and Discovery, 2018, vol. 15, # 4, p. 363 - 374
  • 7
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Reference: [1] Patent: US6582351, 2003, B1,
  • 8
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  • [ 96-99-1 ]
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YieldReaction ConditionsOperation in experiment
>99% With thionyl chloride In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate a)
Preparation of methyl 4-chloro-3-nitrobenzoate
To a solution of 10.0 g (49.6 mmol) of 4-chloro-3-nitrobenzoic acid in 100 ml of methanol was added dropwise 11.8 g (99.2 mmol) of thionyl chloride at 0° C.
The reaction mixture was refluxed for 2 hours and the solvent was then distilled off under reduced pressure.
Ice water was added to the resulting residue.
The mixture was made basic by the addition of concentrated ammonium hydroxide.
The mixture was extracted three times with ethyl acetate.
The combined extracts were washed with water and dried over anhydrous magnesium sulfate.
The solvent was then distilled off under reduced pressure to give 10.9 g (>99percent) of the desired methyl 4-chloro-3-nitro-benzoate.
Reference: [1] Patent: US6169107, 2001, A,
  • 9
  • [ 4731-65-1 ]
  • [ 96-99-1 ]
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Reference: [1] Organometallics, 2016, vol. 35, # 19, p. 3406 - 3412
  • 10
  • [ 1126-46-1 ]
  • [ 14719-83-6 ]
Reference: [1] Patent: US2680730, 1950, ,
[2] Patent: US2680730, 1950, ,
  • 11
  • [ 96-99-1 ]
  • [ 14719-83-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
  • 12
  • [ 74-11-3 ]
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
  • 13
  • [ 67-56-1 ]
  • [ 38818-50-7 ]
  • [ 14719-83-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
  • 14
  • [ 1126-46-1 ]
  • [ 7697-37-2 ]
  • [ 14719-83-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
  • 15
  • [ 14719-83-6 ]
  • [ 64-17-5 ]
  • [ 16588-16-2 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 11, p. 1703 - 1707
  • 16
  • [ 14719-83-6 ]
  • [ 40757-20-8 ]
Reference: [1] Patent: US5844110, 1998, A,
  • 17
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  • [ 41263-74-5 ]
Reference: [1] Patent: WO2014/15905, 2014, A1,
[2] Patent: US2015/175600, 2015, A1,
[3] Patent: WO2016/185279, 2016, A1,
  • 18
  • [ 14719-83-6 ]
  • [ 66315-16-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1587 - 1597
[2] Heterocyclic Communications, 2001, vol. 7, # 5, p. 455 - 460
[3] Patent: US2014/309427, 2014, A1,
[4] Patent: WO2008/65508, 2008, A1,
  • 19
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YieldReaction ConditionsOperation in experiment
96% With sodium acetate In acetonitrile for 7 h; Heating / reflux Methyl 4-chloro-3-nitrobenzoate (72.01 g, 0.334 mol) was suspended in freshly distilled acetonitrile (360 mL) under stirring. Anhydrous sodium acetate (41.1 g, 0.5 mol) and then a 30percent w/w aqueous solution of methylamine (69 mL, 0.67 mol) were added to this suspension under vigorous stirring. The obtained mixture was refluxed for 7 h while the course of the reaction was monitored by TLC (chloroform/CCI4 1 :2). The yellow precipitate was separated by filtration and mixed with a solution of K2CO3 (25 g) in water (500 mL). The mixture was stirred for 30 min and then filtered. The yellow precipitate was washed with water to attain pH 7. The filtrate was concentrated under reduced pressure to a volume of ~200 mL and then mixed with a solution of K2CO3 (5 g) in water (100 mL). The mixture was stirred for 30 min and then filtered. The yellow precipitate was washed with water to attain pH 7. Two above precipitates were combined and dried to give the title compound as a yellow powder in 96percent (67.63 g) yield.
96% With sodium acetate In water; acetonitrileHeating / reflux Methyl 3-nitro-4-chlorobenzoate (72.01 g, 0.334 mol) was suspended in freshly distilled acetonitrile (360 mL) under stirring. Anhydrous sodium acetate (41.1 g, 0.5 mol) and 30percent aqueous solution of methylamine (69 mL, 0.67 mol) were added to this suspension under vigorous stirring. The obtained mixture was refluxed for 7 hours and then kept overnight with TLC monitoring (chloroform/CCL, 1 :2). The yellow precipitate was separated by filtration and mixed with a solution of K2CO3 (25 g) in water (500 mL). The mixture was stirred for 30 minutes and filtered. The yellow precipitate was washed with water to attain pH 7. The filtrate was concentrated under a reduced pressure to a volume of about 200 mL and mixed with a solution_of K2CO3 (5 g) in water (100 mL). The mixture was stirred for 30 minutes and filtered. The yellow precipitate was washed with water to attain pH 7. Two above precipitates were combined and dried to give methyl 4-(methylamino)-3-nitrobenzoate as a yellow powder in (67.63 g, 96percent).4-(Methylamino)-3-nitrobenzoate (63.06 g, 0.3 mol) was suspended under vigorous stirring in methanol (700 mL). A suspension of Raney nickel (15 g, freshly prepared by treatment of nickel- aluminum 50/50 alloy with the 2N NaOH solution) in methanol (30 mL) was added to the suspension. The obtained mixture was heated to 40 45 0C under vigorous stirring, and hydrazine monohydrate (60 mL, 1.2 mol) was added drop wise to the suspension for 3 hours at a temperature below 55 0C. The mixture was stirred at 50 55 0C for 3 hours and kept overnight at room temperature. The reaction mixture was heated again to 40 45 0C under vigorous stirring, and an additional amount of hydrazine hydrate (5 mL) was added to the mixture. The suspension was refluxed for 2 hours under vigorous stirring, cooled, and diluted with chloroform (1 L). The mixture was passed through diatomaceous earth (upper layer 2 cm, diameter 17 cm) and silica gel (lower layer 5 cm) to remove Raney nickel. The layers were washed with chloroform/methanol mixture (1 :1 , 5 * 600 mL). The filtrate was concentrated under a reduced pressure. The residue was diluted with benzene (100 mL), and the mixture was concentrated under a reduced pressure to remove water. This operation was repeated to give methyl 3-amino-4-(methylamino)benzoate <n="34"/>as a brown crystalline solid in (53.6 g, 99percent) which was used in the next stage without additional purification.Methyl 3-amino-4-(methylamino)benzoate (53.6 g, 0.3 mol) was dissolved in anhydrous ' dichloromethane (700 ml_). 1,1 Carbonyldiimidazole (CDI, 62.59 g, 0.386 mol) was added to this solution in several small portions under stirring for 2 hours. The reaction mixture was stirred at room temperature overnight. The formed precipitate was separated by filtration, washed with cold ether (3 * 50-mL), and dried to give methyl 1-methyl-2-oxo-2,3-dihydro-1 H-benzimidazole-5-carboxylate as light-pink crystals in (49.75 g, 81percent ).Phosphoryl bromide (POBr3, 102.4 g, 0.357 mol) was dissolved in dichloroethane (400 mL). Methyl 1- methyl-2-oxo-2,3-dihydro-1 H-benzimidazole-5-carboxylate (36.7 g, 0.178 mol) was added to this solution in several small portions under stirring, and the obtained suspension was refluxed with TLC monitoring (chloroform/1 ,2-dimethoxyethane 10:1). After the reaction was completed (about 19 hour), the reaction mixture was cooled in an ice-bath and carefully neutralized for 3 hours with water (50 mL), and then with a solution of Na2CO3 (100 g) in water (800 mL) intense foaming observed. The quenched mixture was extracted with chloroform (2 L). The layers were separated, and the aqueous layer was extracted again with chloroform (500 mL). The organic layers were combined, washed with water (3 * 250 mL), and dried over CaCI2. The organic solution was concentrated under a reduced pressure. The resulting pale-gray solid was recrystallized from acetonitrile to give methyl 2-bromo-1-methyl-1 H-benzimidazole-5- carboxylate as a white solid in (37.1 g, 77.5percent).A mixture of methyl 2-bromo-1-methyl-1 H-benzimidazole-5-carboxylate (40.0 g, 0.149 mol), pyrrolidine (25.37 g, 30 mL, 0.357 mol), cesium fluoride CsF (31.61 g, 0.208 ml), and DMSO (240 mL) was placed into a microwave reactor (MILESTONE Microwave Labstation; Shelton, CT). The reaction . mixture was treated with microwave radiation under stirring at an internal temperature of 115 0C for 8 h, cooled, and poured into ice-cold water (1 L). The formed precipitate was separated by filtration, washed _withxold w_ater_(2 * 50 mL), he.xane_(2 x 100 mL), and dried. The product was mixed with ether (250 mL) and acetonitrile (20 mL), and the mixture was placed into an ultrasonic bath for 1.5 hours. The precipitate was separated by filtration.-washed with ether (2 * 50 mL), and dried to give methyl 1-methyl-2-pyrrolidin- 1-yl-1 H-benzimidazole-5-carboxylate in (28.82 g, 75percent).A suspension of methyl 1-methyl-2-pyrrolidin-1-yl-1 H-benzimidazole-5-carboxylate (28.8 g, 0.111 mol) "in methahof(200 mL) was rnixed~with a~solQtion~f KOH (12.4'4 g, 0:222 mol) in water (200 mL). The mixture was refluxed for 3 hours and kept overnight at room temperature. The reaction mixture was concentrated under a reduced pressure to remove methanol. The residue was mixed with a solution of KHSO4 (30.21 g, 0.222 mol) in water (200 mL), and the mixture was stirred for 1 hours. The reaction mixture was concentrated under a reduced pressure to dryness, and the product was extracted from the solid residue with a warm mixture of chloroform and isopropanol (1:1 , about 7 L). The obtained extract was concentrated under a reduced pressure, and the residue was dissolved in a boiling mixture of dichloromethane and isopropanol (1 :1 , 500 mL). The solution was refluxed for 30 minutes and cooled in a freezer. The formed precipitate was separated by filtration and dried to give 1-methyl-2-pyrrolidin-1-yl-1H- benzimidazole-5-carboxylic acid as a pale-yellow crystalline solid in (18.3 g, 67percent).
93% at 70 - 90℃; Inert atmosphere Methylamine (2M in THF) (23.19 mL, 46.4 mmol) was added to a solution of methyl 4-chloro-3-nitrobenzoate (5 g, 23.19 mmol) (available, for example, from Lancaster Synthesis Ltd.) inN,N-dimethylformamide (DMF) (8 mL) at rt under nitrogen. The reaction mixture was heated to 80°C and stirred overnight. LCMS showed major peak product, but reaction had not gone to completion. Further methylamine (2M in THF, lOmI) was added and the reaction heated to 90°C for 6 h. Further methylamine (2M in THF, 6m1) was added and the reaction stirredfor 1 h at rt and 72 h at 70°C. Further methylamine (2M in THF, lOmI) was added and the reaction heated to 80°C for 3 h. The reaction was allowed to cool to rt and then the product was precipitated by the addition of water (5OmL). The resultant suspension was cooled to 0°C and then filtered. The residue was washed with further water (3 x 25mL) and allowed to dry on the filter pad for --l5mins. The solid was collected and dried in vacuo to afford thetitle compound as a yellow solid (4.54 g, 21.60 mmol, 93 percent yield). LCMS (Method B): Rt = 0.69 mi MH = 197.2
93% at 20 - 90℃; Inert atmosphere Intermediate 18: Methyl 4-(methylamino)-3-nitrobenzoate
Methylamine (2M in THF) (23.19 mL, 46.4 mmol) was added to a solution of methyl 4-chloro-3-nitrobenzoate (5 g, 23.19 mmol) (available, for example, from Lancaster Synthesis Ltd.) in N,N-dimethylformamide (DMF) (8 mL) at rt under nitrogen.
The reaction mixture was heated to 80° C. and stirred overnight. LCMS showed major peak product, but reaction had not gone to completion.
Further methylamine (2M in THF, 10 ml) was added and the reaction heated to 90° C. for 6 h.
Further methylamine (2M in THF, 6 ml) was added and the reaction stirred for 1 h at rt and 72 h at 70° C.
Further methylamine (2M in THF, 10 ml) was added and the reaction heated to 80° C. for 3 h.
The reaction was allowed to cool to rt and then the product was precipitated by the addition of water (50 mL).
The resultant suspension was cooled to 0° C. and then filtered.
The residue was washed with further water (3*25 mL) and allowed to dry on the filter pad for 15 mins.
The solid was collected and dried in vacuo to afford the title compound as a yellow solid (4.54 g, 21.60 mmol, 93percent yield).
LCMS (Method B): Rt=0.69 min, MH+=197.2
93% at 70 - 90℃; Methylamine (2M in THF) (23.19 mL, 46.4 mmol) was added to a solution of methyl 4- chloro-3-nitrobenzoate (5 g, 23.19 mmol) (available, for example, from Lancaster Synthesis Ltd.) in Ν,Ν-dimethylformamide (DMF) (8 mL) at rt under nitrogen. The reaction mixture was heated to 80 °C and stirred overnight. LCMS showed major peak product, but reaction had not gone to completion. Further methylamine (2M in THF, 10 mL) was added and the reaction heated to 90 °C for 6 h. Further methylamine (2M in THF, 6 mL) was added and the reaction stirred for 1 h at rt and 72 h at 70°C. Further methylamine (2M in THF, 10 mL) was added and the reaction heated to 80 °C for 3 h. The reaction was allowed to cool to rt and then the product was precipitated by the addition of water (50 mL). The resultant suspension was cooled to 0 °C and then filtered. The residue was washed with further water (3 x 25 mL) and allowed to dry on the filter pad for -15 mins. The solid was collected and dried in vacuo to afford the title compound as a yellow solid (4.54 g, 21.60 mmol, 93 percent yield).LCMS (Method B): Rt = 0.69 min, MH+= 197.2
82% at 80℃; for 16 h; Sealed tube Synthesis of benzimidazole ester F-14: 2-[[(4-Methoxy-2,6-dimethyl- phenyOsulfonyll-methyl-aminol-S-methyl-SH-benzoimidazole-δ-carboxylic acid methyl ester (F-14); (I) Methylamine (9.26 mmol, 2 eq.) was added to a solution of methyl 4-choro-3-nitro benzoate (4.6 mmol) in DMF (1.5 ml) and the mixture was heated at 80 0C in a sealed tube for 16 h, subsequently cooled to room temperature and diluted with water. The yellow precipitate formed was filtered off and washed with water, and 3x toluene was added and the mixture evaporated on a rotary evaporator. Yield: 82 percent

Reference: [1] Patent: WO2007/69053, 2007, A1, . Location in patent: Page/Page column 33
[2] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 32-33; 38-40
[3] Patent: WO2014/15905, 2014, A1, . Location in patent: Page/Page column 50
[4] Patent: US2015/175600, 2015, A1, . Location in patent: Paragraph 0389; 0390; 0391
[5] Patent: WO2016/185279, 2016, A1, . Location in patent: Page/Page column 108; 109
[6] Patent: WO2010/142402, 2010, A1, . Location in patent: Page/Page column 112
[7] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 5, p. 1587 - 1597
[8] Heterocyclic Communications, 2001, vol. 7, # 5, p. 455 - 460
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  • [ 14719-83-6 ]
  • [ 593-51-1 ]
  • [ 36242-50-9 ]
Reference: [1] Patent: US2014/309427, 2014, A1, . Location in patent: Paragraph 0166; 0167
  • 21
  • [ 14719-83-6 ]
  • [ 40872-87-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3927 - 3936
[2] Patent: US2680730, 1950, ,
  • 22
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Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 6034,6037
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