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Chemical Structure| 107582-20-7
Chemical Structure| 107582-20-7
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Product Details of [ 107582-20-7 ]

CAS No. :107582-20-7 MDL No. :MFCD04038589
Formula : C8H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BLJHLOLVEXWHFS-UHFFFAOYSA-N
M.W : 166.18 Pubchem ID :571825
Synonyms :

Calculated chemistry of [ 107582-20-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.53
TPSA : 78.34 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 0.65
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.26
Consensus Log Po/w : 0.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 2.27 mg/ml ; 0.0137 mol/l
Class : Very soluble
Log S (Ali) : -2.44
Solubility : 0.601 mg/ml ; 0.00362 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.75
Solubility : 2.97 mg/ml ; 0.0179 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.32

Safety of [ 107582-20-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 107582-20-7 ]

* 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 [ 107582-20-7 ]
  • Downstream synthetic route of [ 107582-20-7 ]

[ 107582-20-7 ] Synthesis Path-Upstream   1~23

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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
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YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol at 20℃; for 48 h; To a nitrogen-saturated solution of 2-amino-3-nitrobenzoic acid methyl ester (Chess GmbH, 50 g, 0.26 mol) in absolute ethanol (800 mL) was added palladium hydroxide (Degussa, 20percent w/w on carbon, 58.75percent w/w water, 10 g).
The slurry was degassed then shaken vigorously under hydrogen (4 atm) at room temperature for 48 h.
The catalyst was filtered and the filtrate concentrated in vacuo to afford 2,3-diaminobenzoic acid methyl ester as a dark orange oil that solidified on standing (43 g, 0.26 mol, 100percent).
(m/z): [M-OCH3]+ calcd for C8H10N2O2 135.05; found 135.3. 1H NMR (300 MHz, DMSO-d6): δ (ppm) 3.74 (s, 3H), 4.80 (br s, 1H), 6.20 (br s, 1H), 6.38 (t, 1H), 6.70 (d, 1H), 7.06 (d, 1H).
100% With hydrogen In ethyl acetate at 20℃; for 48 h; Methyl 2-amino-3-nitrobenzoate (117; 3.2 g) was dissolved in EtOAc (100 mL) and10percent Pd on C (200 mg) was added. The resulting reaction mixture was hydrogenated under 1 atm of hydrogen at room temperature for 2 days and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford essentially quantitative yield of methyl 2,3-diaminobenzoate 118.
100% With hydrogen In ethanol for 24 h; Inert atmosphere 21a) Methyl 2,3-diaminobenzoate10percent Palladium on carbon (0.25 g) was placed in a 3-neck round bottom flask then flushed with nitrogen and evacuated. This was repeated several times, then ethanol (100 mL) was added to the flask. Partially dissolved methyl 2-amino-3- nitrobenzoate (3.5 g, 17.8 mmol) in ethanol (60 mL) was added, and the reaction mixture purged with nitrogen and evacuated. The reaction mixture was left to stir under hydrogen (1.6 L). After stirring for 24 h, the reaction mixture was filtered over a pad of Celite.(R)., washed with ethanol and the filtrate was concentrated to afford 3.4 g (100percent) of methyl 2,3-diaminobenzoate. 1H NMR (400 MHz, d6-DMSO): δ 7.07 (dd, J = 8, 1 Hz, IH), 6.67 (m, IH), 6.36 (t, J = 8 Hz, IH), 6.17 (br s, 2H), 4.74 (br s, 2H), 3.73 (s, 3H).
100% With hydrogen In methanol at 20℃; for 12 h; (4)
methyl 3-aminoanthranilate
To a solution of methyl 3-nitroanthranilate (1.44 g, 7.34 mmol) in methanol (50 ML) was added 10percentPd/C (300 mg), and the resulting mixture was stirred for 12 hours at room temperature under hydrogen atmosphere..
The 10percentPd/C was removed, and the solvent was distilled off under reduced pressure, to give 1.22 (quantitative yield) of the desired compound in the form of a brown crystalline product.
99% With hydrogen In tetrahydrofuran at 20℃; for 4 h; Reference Example 3
Methyl 2,3-diaminobenzoate (Method 2)
To a solution of methyl 2-amino3-nitrobenzoate (29.6 g, 151 mmol) in tetrahydrofuran (containing stabilizer; 500 mL) was added palladium on carbon (3.0 g), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 4 hr.
The catalyst was removed by filtration, and the filtrate was concentrated in vacuo.
The residual solid was washed with diethyl ether-n-hexane to give the title compound (25.0 g, 150 mmol, >99percent) as a pale yellow solid.
1H NMR (CDCl3) δ: 3.33 (2H, brs), 3.07 (3H, s), 5.56 (2H, brs), 6.60 (1H, dd, J=8.1, 7.5 Hz), 6.85 (1H, dd, J=7.5, 1.5 Hz), 7.47 (1H, dd, J=8.1, 1.5 Hz).
MS Calcd.: 166; MS Found: 167 (M+H).
99% With hydrogen In ethanol at 20℃; for 16 h; Methyl 2-amino-3-nitrobenzoate (10 g, 51 mmol) was dissolved in ethanol (500 mL)under nitrogen. Palladium on carbon (10percent w/w, 2.7 g, 2.6 mmol) was added undernitrogen. The reaction was placed under a hydrogen atmosphere (1 atm) and stirredfor 16 h at room temperature. The reaction was flushed with nitrogen, filtered throughdiatomaceous earth and concentrated to provide the product (8.39 g, 99percent) as awhite solid. 1H-NMR (DMSO-6) 6 7.07 (d, J = 8.1 Hz, 1H), 6.68 (d, J = 8.1 Hz, 1H),6.37 (t, J = 8.1 Hz, 1H), 6.18 (brs, 2H), 4.75 (brs, 2H), 3.74 (s, 3H).
98% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol; water at 20℃; for 3 h; 2) 10percent Palladium carbon (water content 51.7percent, 250 mg) was added to a solution of methyl ester of 2-amino-3-nitrobenzoic acid (980 mg, 5.00 mmol) in methanol (20 ml)-tetrahydrofuran (10 ml) and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hrs. The catalyst was removed by filtration and washed with tetrahydrofuran. The filtrate and washings were combined and the solvent was distilled off under reduced pressure to give methyl ester of 2,3-diaminobenzoic acid (814 mg, 98percent) as a yellowish green solid. m.p.: 65-67° C.; IR (Nujol) : 3451, 3314, 1701, 1619 cm-1; APCI-MS m/z: 167 [M+H]+
97% With tin(II) chloride dihdyrate In methanol at 65℃; for 16 h; Inert atmosphere Tin(II)chloride dihydrate (17.25 g, 76.5 mmol) was added in one portion to methyl 2-amino-3-nitrobenzoate (5.0 g, 25.5 mmol) in methanol (100 mL) under nitrogen. The yellow mixture was vigorously stirred at 65 0C for 16 h, and the solvent was removed by rotary evaporation to near dryness. The residue was taken up in EtOAc and the solution was poured into a large beaker containing 1 : 1 EtOAc/NaHCψ3 soln (300 mL) and stirred 15 min. The precipitates were removed by filtration and the organic layer was separated. The aqueous layer was extracted twice more with EtOAc, and the combined organic layer was washed with saturated NaHCO3 solution, brine, dried (Na2SO4), and filtered. Concentration of the filtrate gave methyl 2,3-diaminobenzoate as a deep red viscous oil (4.1 g, 97percent).
95% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24 h; Methyl 2-amino-3-nitrobenzoate (2.5g, 12.75mmol) dissolved in 20mL methanol, Palladium-carbon (500 mg) was added. The mixture was stirred at room temperature under a hydrogen atmosphere for 24 h, palladium on carbon was removed by filtration, the filtrate was concentrated, and the residue was subjected to column chromatography to give the titled compound (2 g, yield 95percent) as a brown solid
94% at 50℃; for 0.5 h; 2-amino-3-nitrobenzoic acidMethyl ester (Z-1)(500 mg, 2.78 mmol, commercially available compound) was added acetic acid (10 mL)After heating to 50 ° C, zinc powder (1.67 g, 25.5 mmol) was added,Stir for 30 minutes.The reaction solution was allowed to cool,After filtering the zinc powder,The solvent was distilled off under reduced pressure,To the resulting residue was added ethyl acetate (15 mL) and saturated aqueous sodium bicarbonate (15 mL) and extracted.The organic layer was washed successively with water (15 mL) and saturated brine (15 mL)After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure,To give the title compound (9-1) (391 mg, yield 94percent).
94% at 50℃; for 0.5 h; Production of Methyl 2,3-Diaminobenzoate (9-1)
To methyl 2-amino-3-nitrobenzoate (Z-1) (500 mg, 2.78 mmol, commercially available compound), acetic acid (10 mL) was added, followed by heating to 50° C. Then, zinc powder (1.67 g, 25.5 mmol) was added, followed by stirring for 30 minutes.
After the reaction liquid was allowed to cool, the zinc powder was removed by filtration, and then the solvent was removed by evaporation under reduced pressure.
To the obtained residue, ethyl acetate (15 mL) and saturated aqueous sodium hydrogen carbonate (15 mL) were added, followed by extraction.
The organic layer was washed sequentially with water (15 mL) and with saturated aqueous sodium chloride (15 mL), and dried over anhydrous magnesium sulfate.
Then, the solvent was removed by evaporation under reduced pressure to obtain the title compound (9-1) (391 mg, yield: 94percent).
92% With hydrogen In methanol for 1 h; After dissolving 2-amino-3-nitrobenzoic acid methyl ester (661 mg, 3.37 mmol) in methanol (30 ml), 10percent palladium-carbon powder (5 molpercent) was added under a nitrogen stream, and the mixture was stirred for 1 hour under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate = 2/1) to obtain 2,3-diaminobenzoic acid methyl ester. The compound was identified by NMR. Yield: 517.2 mg (92percent).1H-NMR (270 MHz, CDCl3): δ7.46(1H,dd,J=8.2Hz,1.5Hz), 6.85(1H,dd,J=8.2Hz,1.5Hz), 6.60(1H,t,J=8.2Hz), 5.53(br), 3.87(3H,s), 3.35(br) ppm.
91% With hydrogen In methanol at 20℃; for 20 h; To a suspension of methyl 2-amino-3-nitrobenzoate (15 g, 76.5 mmol) in methanol (800 mL) was added 10percent palladium on carbon (50percent wet; 6.5 g) , and the mixture was stirred at room temperature for 20 hours under hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residual solid was crystallized from diisopropyl ether-hexane to give 11.57 g (69.6 mmol, 91.0percent) of the title compound as a dark yellow needle .1H NMR (CDCl3) δ: 3.33 (2H, br s) , 3.07 (3H, s) , 5.56 (2H, br s), 6.60 (IH, dd, J = 8.1, 7.5 Hz), 6.85 (IH, dd, J = 7.5, 1.5 Hz), 7.47 (IH, dd, J= 8.1, 1.5 Hz). MS Calcd. : 166; Found: 167 (M+H) .
90% With hydrogen In methanol for 3 h; (IV) The product just obtained in stage (III) (30 g), in methanol (1.5 I), was hydrogenated for 3 h using 10 percent Pd/C (3 g). The reaction mixture was filtered and concentrated to obtain the desired product. Yield: 90 percent
88% With hydrogen In methanol for 8 h; Step 5: 2,3-Diamino-benzoic acid methyl ester ; To a solution of 2-amino-3-nitro-benzoic acid methyl ester (2 g, 10 mmol) in methanol, a suspension of 10percent Pd/C (300 mg) in methanol 5 ml. was added and hydrogenated with a hydrogen balloon over a period of 8 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain 1.5 g of the required compound as a brown coloured solid (88percent).1H NMR (300 MHz, DMSOd6): δ (ppm) = 7.09(dd, 1 H, J=8.1 ; 1.2 Hz), 6.70(dd, 1 H, J=8.1 ; 1.2 Hz), 6.3.8(m, 1 H), 6.199(s, 2H), 4.77(s, 2H), 3.76(s, 3H).

Reference: [1] Patent: US2006/270652, 2006, A1, . Location in patent: Page/Page column 14
[2] Patent: WO2010/3048, 2010, A1, . Location in patent: Page/Page column 117
[3] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 126
[4] Patent: EP1452528, 2004, A1, . Location in patent: Page 22
[5] Patent: US2009/186879, 2009, A1, . Location in patent: Page/Page column 50
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5048 - 5052
[7] Patent: WO2006/23400, 2006, A2, . Location in patent: Page/Page column 53-54
[8] Patent: EP2959918, 2015, A1, . Location in patent: Paragraph 0103
[9] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5023 - 5026
[10] Patent: WO2010/17401, 2010, A1, . Location in patent: Page/Page column 141
[11] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[12] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1212 - 1216
[13] Patent: CN103570683, 2018, B, . Location in patent: Paragraph 0463; 0464; 0469-0471
[14] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[15] Patent: CN105473557, 2016, A, . Location in patent: Paragraph 0247-0251
[16] Patent: US2016/200690, 2016, A1, . Location in patent: Paragraph 0136; 0137
[17] Patent: EP1502916, 2005, A1, . Location in patent: Page 435
[18] Patent: WO2006/116412, 2006, A2, . Location in patent: Page/Page column 163
[19] Patent: WO2010/142402, 2010, A1, . Location in patent: Page/Page column 109-110
[20] Patent: WO2010/115736, 2010, A2, . Location in patent: Page/Page column 62-63
[21] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
[22] Patent: US2003/191116, 2003, A1,
[23] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 119 - 124
[24] Patent: US2003/207868, 2003, A1,
[25] Patent: US6100283, 2000, A,
[26] Patent: WO2008/15429, 2008, A2, . Location in patent: Page/Page column 55-56
[27] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7170 - 7185
[28] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 15; 16
[29] Patent: WO2007/51062, 2007, A2, . Location in patent: Page/Page column 132-133
[30] Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926
[31] Patent: CN104876877, 2018, B, . Location in patent: Paragraph 0033; 0059-0068
[32] Patent: WO2007/113596, 2007, A1, . Location in patent: Page/Page column 84
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YieldReaction ConditionsOperation in experiment
98% With hydrogen In tetrahydrofuran; methanol at 20℃; for 3 h; 10 percent Palladium carbon (water content 51.7 percent, 250 mg) was added to a solution of methyl ester of 2-amino-3-nitrobenzoic acid (980 mg, 5.00 mmol) in methanol (20 ml)-tetrahydrofuran (10 ml) and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hrs. The catalyst was removed by filtration and washed with tetrahydrofuran. The filtrate and washings were combined and the solvent was distilled off under reduced pressure to give methyl ester of 2,3-diaminobenzoic acid (814 mg, 98percent) as a yellowish green solid. m.p.: 65 - 67°C; IR (Nujol): 3451, 3314, 1701, 1619 cm-1; APCI-MS m/z: 167 [M+H]+
Reference: [1] Patent: EP1481965, 2004, A1, . Location in patent: Page 27-28
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YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 20℃; for 3 h;
Stage #2: With sodium hydrogencarbonate In water
Reference Example 2
Methyl 2,3-diaminobenzoate (Method 1)
Methyl 3-amino-2[(tert-butoxycarbonyl)amino]benzoate (61.8 g, 232 mmol) was added to trifluoroacetic acid (250 mL), and the mixture was stirred at room temperature for 3 hr.
Trifluoroacetic acid was evaporated in vacuo, and the resulting solid was suspended in ethyl acetate (200 mL), collected by filtration and washed with ethyl acetate (50 mL).
The solid was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium hydrogen carbonate (400 mL), and the aqueous layer was seated and extracted with ethyl acetate (300 mL).
The combined organic layer was washed with water (300 mL*2) and concentrated in vacuo to give the title compound (24.6 g, 148 mmol, 64percent) as a brown solid.
The filtrate described above was concentrated in vacuo, and the resulting solid was collected by filtration and washed with ethyl acetate.
The filtrate was concentrated in vacuo, and the resulting solid was collected by filtration and washed with diethyl ether.
The combined solid was partitioned between ethyl acetate (100 mL) and saturated aqueous sodium hydrogen carbonate (100 mL), and the aqueous layer was seated and extracted with ethyl acetate).
The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (8.29 g, 49.9 mmol, 22percent) as a brown solid.
Total amount: 32.9 g, 198 mmol, 85percent.
1H NMR (CDCl3) δ: 3.33 (2H, brs), 3.07 (3H, s), 5.56 (2H, brs), 6.60 (1H, dd, J=8.1, 7.5 Hz), 6.85 (1H, dd, J=7.5, 1.5 Hz), 7.47 (1H, dd, J=8.1, 1.5 Hz).
MS Calcd.: 166; MS Found: 167 (M+H).
Reference: [1] Patent: US2009/186879, 2009, A1, . Location in patent: Page/Page column 50
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Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 119 - 124
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[4] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
[5] Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926
[6] Patent: EP1452528, 2004, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1212 - 1216
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 119 - 124
[5] Patent: EP2959918, 2015, A1,
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Reference: [1] Patent: US2003/22883, 2003, A1,
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Reference: [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 8, p. 2297 - 2304
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Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
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Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 119 - 124
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Reference: [1] Patent: US6100283, 2000, A,
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Reference: [1] Patent: EP1452528, 2004, A1,
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Reference: [1] Patent: EP1452528, 2004, A1,
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Patent: CN104876877, 2018, B,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5023 - 5026
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YieldReaction ConditionsOperation in experiment
83.1% at 25 - 35℃; for 2 - 3 h; Methyl 2-amino-3-nitrobenzoate (150.0 grams, 0.765 moles) was placed inan autoclave vessel and 1000 mlof ethyl acetate and 75 grams of Raney nickelwere added to the vessel and stirred under a 2-3 kg/cm2 hydrogen pressure for12-15 hours. The catalyst was removed by filtration, and the ethyl acetate wasevaporated under reduced pressure. Acetic acid (170 ml) was added to theresidue, and 180 grams of tetraethylorthocarbonate was slowly added at 25-35°C.The reaction mass was stirred for 2-3 hours, and water (750 ml) was added afterthe reaction mass was cooled to 10°C. The solid was filtered, washed with 150 mlof water, and dried at 50-60°C to get 140 grams (83.1 percent) of methyl 2-ethoxybenzimidazole-7-carboxylate.; 150 grams of 2-Amino-3-nitro-benzoic acid methylester, Raney nickel (75grams), ethyl acetate (1 litre) were charged in an autoclave vessel. 3.0kg/cm2 ofdry hydrogen gas was passed into the reaction suspension for about 20-25 hoursunder agitation. Reaction mass was filtered on celite, followed by washing thecelite with 150 ml of ethyl acetate. Solvent was removed completely from thefiltrate at about 45-50°C by distillation. 171 ml of acetic acid was charged andtetraethylorthocarbonate (180 grams) was added over about 30-45 minutes.Reaction mass was maintained for about 1-3 hours and was cooled to about 0-5°C. 750 ml of water was added over about 15-30 minutes and the separatedsolid was filtered and washed with 150 ml water, followed by 150 ml of ethylacetate. Solid obtained was dried at about 55-65°C for about 10-12 hours to yield140 grams of 2-Ethoxy-3H-benzoimidazole-4-carboxylic acid methylestercompound of Formula (IV).
Reference: [1] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 15; 16
[2] Patent: CN104876877, 2018, B, . Location in patent: Paragraph 0033; 0069-0072
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Methyl 4-amino-3-formylbenzoate

Similarity: 0.96

Chemical Structure| 18595-16-9

[ 18595-16-9 ]

Methyl 2-amino-5-methylbenzoate

Similarity: 0.96

Chemical Structure| 619-45-4

[ 619-45-4 ]

Methyl 4-aminobenzoate

Similarity: 0.92

Chemical Structure| 40800-65-5

[ 40800-65-5 ]

Ethyl 4-amino-3-methylbenzoate

Similarity: 0.91

Chemical Structure| 18595-12-5

[ 18595-12-5 ]

Methyl 5-amino-2-methylbenzoate

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Esters

Chemical Structure| 841296-15-9

[ 841296-15-9 ]

Methyl 4-amino-3-formylbenzoate

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Chemical Structure| 18595-16-9

[ 18595-16-9 ]

Methyl 2-amino-5-methylbenzoate

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Chemical Structure| 619-45-4

[ 619-45-4 ]

Methyl 4-aminobenzoate

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Chemical Structure| 40800-65-5

[ 40800-65-5 ]

Ethyl 4-amino-3-methylbenzoate

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Chemical Structure| 18595-12-5

[ 18595-12-5 ]

Methyl 5-amino-2-methylbenzoate

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Amines

Chemical Structure| 841296-15-9

[ 841296-15-9 ]

Methyl 4-amino-3-formylbenzoate

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Chemical Structure| 18595-16-9

[ 18595-16-9 ]

Methyl 2-amino-5-methylbenzoate

Similarity: 0.96

Chemical Structure| 619-45-4

[ 619-45-4 ]

Methyl 4-aminobenzoate

Similarity: 0.92

Chemical Structure| 40800-65-5

[ 40800-65-5 ]

Ethyl 4-amino-3-methylbenzoate

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Chemical Structure| 18595-12-5

[ 18595-12-5 ]

Methyl 5-amino-2-methylbenzoate

Similarity: 0.90