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[ CAS No. 190728-25-7 ] {[proInfo.proName]}

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Chemical Structure| 190728-25-7
Chemical Structure| 190728-25-7
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Product Details of [ 190728-25-7 ]

CAS No. :190728-25-7 MDL No. :MFCD19685633
Formula : C17H16N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VXEQRXJATQUJSN-UHFFFAOYSA-N
M.W : 296.32 Pubchem ID :11594543
Synonyms :
Chemical Name :4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline

Calculated chemistry of [ 190728-25-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.12
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 85.65
TPSA : 66.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.71
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 3.63
Log Po/w (MLOGP) : 1.62
Log Po/w (SILICOS-IT) : 2.84
Consensus Log Po/w : 2.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.044 mg/ml ; 0.000148 mol/l
Class : Soluble
Log S (Ali) : -4.04
Solubility : 0.0269 mg/ml ; 0.0000908 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.84
Solubility : 0.000423 mg/ml ; 0.00000143 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.33

Safety of [ 190728-25-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 190728-25-7 ]

* 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 [ 190728-25-7 ]
  • Downstream synthetic route of [ 190728-25-7 ]

[ 190728-25-7 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 190728-24-6 ]
  • [ 190728-25-7 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium chloride; zinc In tetrahydrofuran; methanol; water for 2 h; Heating / reflux Step 2:
4-(6,7-dimethoxyquinolin-4-yloxy)aniline (99)
To 98 (0.25 g, 0.77 mmol) in 1:1 MeOH/THF (50 mL) was added Zn dust (0.55 g, 8.4 mmol) and ammonium chloride (0.085 g, 1.6 mmol) in water (5 mL).
The resulting mixture was heated to reflux for 2 h, then filtered through celite and concentrated.
The residue was dissolved in dichloromethane, washed with water, brine, dried (MgSO4), filtered and concentrated to provide crude 99 (0.25 g, >100percent) which was used without further purification. MS (m/z): 297.1 (M+H).
95% With raney nickel In methanol at 30℃; for 10 h; Autoclave Step three:500 ml of methanol was added to the autoclave, and 100 g of intermediate 2 and 25 g of Raney nickel were added.Raise the temperature at 30 ° C for 10 hours;Press filtration, concentration, crystallization, filtration, and drying gave 86 g of Intermediate 3 in a yield of 95percent.
22.4% With palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 73℃; for 12 h; To a suspension of 6,7-dimethoxy-4-(4-nitrophenoxy)quinoline (28 g, 85.8 mmol) and HCOOK (50.5 g, 601.1 mmol) in THF (150 niL) and H20 (40 niL) was added Pd/C (2.8 g, 10percent). The reaction was heated to 73 °C for 12 hours, and then cooled to rt. The organic phase was separated and concentrated in vacuo. The residue was stirred in EtOH (90 mL) and 0 (30 mL) overnight and then collected through filtration to give the title compound as a pale yellow solid (5.7 g, 22.4percent). MS (ESI, pos. ion) m/z: 297.1 [M + H]+; NMR (400 MHz, DMSO-i): δ 3.92 (s, 3H), 3.93 (s, 3H), 5.16 (s, 2H), 6.36 (d, J = 5.2 Hz, 1H), 6.65-6.68 (m, 2H), 6.91-6.93 (m, 2H), 7.36 (s, 1H), 7.50 (s, 1H), 8.42 (d, J = 5.3 Hz, 1H).
3.0 kg With formic acid; palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 60℃; for 15 h; Large scale Preparation of 4—(6,7 —Dimethoxy—quinoline-4—yloxy)--phenylamine[00258J A solution containing potassium formate (5.0 kg), formic acid (3.0 kg), and water (16.0 kg) was added to a mixture of 6,7-dimethoxy-4-(4-nitro-phenoxy)-quinoline (4.0 kg), 10 percent palladium on carbon (50 percent water wet, 0.4 kg) in tetrahydrofuran (TUF, 40.0 kg) that had been heated to approximately 60 °C. The addition was carried out such that the temperature of the reaction mixture remained approximately 60 °C. When the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining, typically 1 5 hours), the reactor contents were filtered. The filtrate was concentrated by vacuum distillation at approximately 35 °C to half of its original volume, which resulted in the precipitation of the product The product was recovered by ifitration, washed with water (12.0 kg), and dried under vacuum at approximately 50 °C to afford the title compound (3.0 kg; 97 percent area under curve (AUC)).
3 kg With formic acid; palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 60℃; for 15 h; Large scale Preparation of 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylamine
A solution containing potassium formate (5.0 kg), formic acid (3.0 kg), and water (16.0 kg) was added to a mixture of 6,7-dimethoxy-4-(4 nitro-phenoxy)-quinoline (4.0 kg), 10percent palladium on carbon (50percent water wet, 0.4 kg) in tetrahydrofuran (40.0 kg) that had been heated to approximately 60° C.
The addition was carried out such that the temperature of the reaction mixture remained approximately 60° C.
When the reaction was deemed complete as determined using in-process HPLC analysis (<2percent starting material remaining, typically 1 5 hours), the reactor contents were filtered.
The filtrate was concentrated by vacuum distillation at approximately 35° C. to half of its original volume, which resulted in the precipitation of the product.
The product was recovered by filtration, washed with water (12.0 kg), and dried under vacuum at approximately 50° C. to afford the title compound (3.0 kg).
3.0 kg With formic acid; palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 60℃; for 1.5 h; Large scale Preparation of 4-(6,7 -Dimethoxy-quinoline-4-yloxy)-phenylamine
A solution containing potassium formate (5.0 kg), formic acid (3.0 kg), and water (16.0 kg) was added to a mixture of 6,7-dimethoxy-4-(4-nitro-phenoxy)-quinoline (4.0 kg), 10 percent palladium on carbon (50 percent water wet, 0.4 kg) in tetrahydrofuran (THF, 40.0 kg) that had been heated to approximately 60 °C.
The addition was carried out such that the temperature of the reaction mixture remained approximately 60 °C.
When the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining, typically 1 5 hours), the reactor contents were filtered.
The filtrate was concentrated by vacuum distillation at approximately 35 °C to half of its original volume, which resulted in the precipitation of the product.
The product was recovered by filtration, washed with water (12.0 kg), and dried under vacuum at approximately 50 °C to afford the title compound (3.0 kg; 97 percent area under curve (AUC)).
86.3 mg With palladium 10% on activated carbon; hydrogen In N,N-dimethyl acetamide at 30 - 40℃; Autoclave 100 g (0.306 mol) of 6,7-dimethoxy-4-(4-nitrophenoxy) quinoline was treated with 300 g N, N-diethylacetamide was dissolved in an autoclave, and 10percent Pd / C 15g was added to react at 30 to 40 ° C under a hydrogen pressure of 2.8 MPa, and the reaction was complete when no hydrogen was absorbed. After removing most of the solvent, the mixture was poured into 150 ml of water and stirred for 1 hour. The precipitated solid particles were filtered and the cake was washed twice with 100 ml of water, dried at 60 ° C,A solution of 4-(6,7- dimethoxyquinolin-4-oxy)phenylamine (86.3 g), molar yield 95.2percent

Reference: [1] Patent: US2008/4273, 2008, A1, . Location in patent: Page/Page column 86
[2] Patent: CN108264482, 2018, A, . Location in patent: Paragraph 0022; 0027
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 23, p. 5117 - 5133
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 1, p. 11 - 17
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6277 - 6292
[6] Patent: WO2013/180949, 2013, A1, . Location in patent: Paragraph 0172
[7] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 875 - 879
[8] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1359 - 1366
[9] Patent: WO2008/48375, 2008, A1, . Location in patent: Page/Page column 48
[10] Patent: WO2010/83414, 2010, A1, . Location in patent: Page/Page column 25
[11] Patent: US2012/70368, 2012, A1,
[12] Patent: US2012/252840, 2012, A1,
[13] Patent: WO2015/164869, 2015, A1, . Location in patent: Paragraph 00255; 00258
[14] Patent: US2016/772, 2016, A1, . Location in patent: Paragraph 0086; 0090
[15] Patent: EP2758057, 2017, B1, . Location in patent: Paragraph 0109
[16] Patent: CN103664778, 2017, B, . Location in patent: Paragraph 0054; 0055; 0056; 0061; 0062
  • 2
  • [ 35654-56-9 ]
  • [ 123-30-8 ]
  • [ 190728-25-7 ]
YieldReaction ConditionsOperation in experiment
83.6% With sodium methylate In dimethyl sulfoxide at 90℃; for 9 h; 4-Chloro-6,7-dimethoxyquinoline (35.3 g, 157.8 mmol) andSodium methoxide (12.1 g, 224 mmol) was addedDimethyl sulfoxide (200 ml). 4-Aminophenol (20.67 g, 189.4 mmol)In dimethylsulfoxide (150 ml) was addedIn the reaction solution, the reaction solution was reacted at 90 ° C for 9 hours, cooled to room temperature, poured into 1600 ml of ice water, and added with 100 mlEthyl acetate, filtered and dried under reduced pressure to give 4 - [(6,7-dimethoxyquinolin-4-yl) oxy] aniline (39.1 g, yield:83.6percent).
74.6%
Stage #1: With sodium hydride In dimethyl sulfoxide at 20℃; for 0.166667 h;
Stage #2: at 100℃; for 3 h;
For 100 ml is added to a round bottom flask NaH (3.3g, 82 . 5mmol) and anhydrous DMSO, after fully stirring, add the aminophenol (6g, 55mmol), stirring the mixture at room temperature for 10 min, then add 4-chloro-6,7-dimethoxy quinoline (12.3g, 55 . 1mmol) in the 100 degrees stirring 3h, TLC monitoring, after the reaction, water, chloroform extraction, the extraction liquid to be grey solid 12.2g, yield 74.6percent.
74.8% at 100℃; for 9 h; To a 1L three-necked flask was added 4-chloro-6,7-dimethoxy-quinoline 35. 3g (157. 8mmol), sodium tert-butoxide21.4g (224. Lmmol) and N,N-dimethylacetamide 200ml, stirred for standby.The N, N- dimethylacetamide 200ml 4-aminophenol with 24. 5g (224. Lmmol) mixed, added to the aboveAlternate reaction solution was added dropwise to control the temperature less than 25 ° C, the dropwise addition, temperature was raised to 100 ° C, the reaction nine hours, the reaction was stopped,Cooling to 15~20 ° C, the reaction mixture was poured into 1600ml ice water, controlling the temperature 15~30 ° C, was added 100ml ethyl Esters, solid separated stirring, suction filtered, the solid washed with ethyl acetate lml, blast drying at 40 ° C for 12 hours to give a brown solid 35g (74. 8percent)
61% With caesium carbonate In dimethyl sulfoxide at 100℃; for 18 h; A suspension of 4-chloro-6, 7-dimethoxyquinoline (1566 mg, 7.00 mmol), 4-aminophenol (917 mg, 8.40 mmol) and cesium carbonate (4561 mg, 14.0 mmol) in dimethyl sulfoxide (14 ml) <n="221"/>was stirred at 1000C for 18 hr. Water was added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate/tetrahydrofuran (=1/1) . .bul. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-methyl acetate/methanol=60/40) . Ethyl acetate was added to the obtained residue and the mixture was filtrated to give the title compound (1267 mg, 61percent) as a white powder.1H-NMR (DMSO-d6, 300 MHz) δ 3.93 (6H, s) , 5.16 (2H, s) , 6.37 (IH, d, J = 5.4 Hz), 6.67 (2H, d, J = 8.7 Hz), 6.93 (2H, d, J= 8.7 Hz), 7.36 (IH, s) , 7.50 (IH, s), 8.43 (IH, d, J = 5.4Hz) .
34.0 kg With sodium t-butanolate In N,N-dimethyl acetamide at 100 - 105℃; for 13 h; Large scale 4-Aminophenol (24.4 kg) dissolved in Ν,Ν-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t- butoxide (21.4 kg) and DMA (167.2 kg) at 20-25 °C. This mixture was then heated to 100- 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining), the reactor contents were cooled at 15-20 °C and water (pre-cooled, 2-7 °C, 587 L) charged at a rate to maintain 15-30 °C temperature . The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg) and finally with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7-dimethoxy-quinoline-4- yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7- dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately Ihour and then cooled to 0-5 °C and aged for approximately 1 hour after which time the solid was filtered, washed with THF ( 147.6 kg) and dried on a filter under vacuum at approximately 25 "C to yield 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylamine (34.0 kg).
34 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 13 h; Large scale [00120] 4-Aminophenol (24.4 kg) dissolved in Ν,Ν-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t- butoxide (21.4 kg), and DMA (167.2 kg) at 20 - 25 °C. This mixture was then heated to 100 - 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2percent starting material remaining), the reactor contents were cooled at 15 to 20 °C and water (pre-cooled, 2 to 7 °C, 587 L) charged at a rate to maintain 15 to 30 °C temperature . The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg) and finally with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7 -dimethoxy-quinoline- 4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7 - dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately 1 hour and then cooled to 0 to 5 °C and aged for approximately 1 hour after which time the solid was filtered, washed with THF (147.6 kg) and dried on a filter under vacuum at approximately 25 °C to yield 4-(6, 7 -dimethoxy-quinoline-4-yloxy)-phenylamine (34.0 kg).
34.0 kg With sodium t-butanolate In N,N-dimethyl acetamide at 100 - 105℃; for 13 h; Large scale Preparation of 4—(6, 7 —Dimethoxy_quinoline_4_yloxy)....phenylamjne [00115] 4-Aminophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium tbutoxide (21.4 kg) and DMA (167.2 kg) at 20-25 °C. This mixture was then heated to 100- 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining), the reactor contents were cooled at 15-20 °C and water (pre-cooled, 2-7 °C, 587 L) charged at a rate to maintain 15-30 °C temperature. The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg) and finally with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7-dimethoxy-quinoline-4- yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7- dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately lhour and then cooled to 0—5 °C and aged for approximately 1 hour after which time the solid was filtered, washed with THF (147.6 kg) and dried on a filter under vacuum at approximately 25 °C to yield 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylam me (34.0 kg).
34 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 13 h; Large scale 4-Aminophenol (24.4 kg) dissolved in Ν,Ν-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t- butoxide (21.4 kg), and DMA (167.2 kg) at 20 - 25 °C. This mixture was then heated to 100 - 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2percent starting material remaining), the reactor contents were cooled at 15 to 20 °C, and water (pre-cooled, 2 to 7 °C, 587 L) was charged at a rate to maintain 15 to 30 °C temperature . The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg), and finally washed with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7 - dimethoxy-quinoline-4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7 ^imethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately 1 hour, then cooled to 0 to 5 °C, and aged for approximately 1 hour, after which time the solid was filtered, washed with THF (147.6 kg), and dried on a filter under vacuum at approximately 25 °C to yield 4-(6, 7 -dimethoxy-quinoline-4-yloxy)- phenylamine (34.0 kg).
34 kg With sodium t-butanolate In N,N-dimethyl acetamide at 100 - 105℃; for 13 h; Large scale 4-Aminophenol (24.4 kg) dissolyed in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium tbutoxide (21.4 kg), and DMA (167.2 kg) at 20—25 °c. This mixture was then heated to 100— 105 °c for approximately 13 hours. After the reaction was deemed complete as determmed using in-process HPLC analysis (less than 2percent starting materia remaining), the reactor contents were cooled at 15 to 20 °c, and water (pre-cooled, 2 to 7 °c, 587 L) was charged at a rate to maintain 15 to 30 °c temperature. The resulting solid precipitate was fultered, washed with a mixture of water (47 L) and DMA (89.1 kg), and fmally washed with water (214 L). The futer cake was then dried at approximately 25 °C on futer to yield crude 4—(6, 7— dimethoxy—quinoline--1---yloxy)—phenylamine (59.4 kg wet, 41.6 kg di3” calculated based on limit of detection, hereinafter LOD”). Crude 4—(6, 7 —dimethoxy—quinoline—4—yloxy)— phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 2 11.4 kg) and DMA (108.8 kg) for approximately 1 hour, then cooled to O to 5 °C, and aged for approximately 1 hour, after which time the solid was fultered, washed with THF (147.6 kg), and dried on a futer under yacuum at approximatey 25 °c to yield 4—(6, 7 —dimethoxy— quinoline—4—yloxy)—phenylamine (3 4.0 kg).
34.0 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 13 h; Preparation of 4—(6, 7 —Dimethoxy--quinoline-4—yloxy)—phenylamiue[002651 4-Antinophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t-butoxide (21.4 kg) and DMA (167.2 kg) at 20-25 °C. This mixture was then heated to 100-105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining), the reactor contents were cooled at 15-20 °C and water (pre-cooled, 2-7 °C, 587 L) charged at a rate to maintain 15-30 DC temperature . The resulting solid precipitate was ifitered, washed with a mixture of water (47 L) and DMA (89.1 kg) and finally with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7-dimethoxy-quinoline-4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7-dimethoxy-quinoline-4- yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately lhour and then cooled to 0—5 °C and aged for approximately 1 hour after which time the solid was filtered, washed with THF (147.6 kg) and dried on a filter under vacuum at approximately 25 °C to yield 4-(6,7-dimethoxy-quinoline-4- yloxy)-phenylamine (34.0 kg).
34.0 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 13 h; Large scale [00114] 4-Aminophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium tbutoxide (21.4 kg), and DMA (167.2 kg) at 20 to 25 °C. This mixture was then heated to 100 to 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process 1-IPLC analysis (less than 2percent starting material remaining), the reactor contents were cooled at 15 to 20 °C, and water (pre-cooled, 2 to 7 °C, 587 L) was charged at a rate to maintain 15 to 30 °C temperature. The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg), and finally washed with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7 -dimethoxy-quinoline-4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on limit of detection, hereinafter “LOU’). Crude 4-(6, 7 -dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (TI-IF, 211.4 kg) and DMA (108.8 kg) for approximately 1 hour, then cooled to 0 to 5 DC, and aged for approximately 1 hour, after which time the solid was filtered, washed with THF (147.6 kg), and dried on a filter under vacuum at approximately 25 °C to yield 4-(6, 7 - dimethoxy-quinoline-4-yloxy)-phenylamine (34.0 kg).
34 kg for 13 h; Large scale 4-Aminophenol (24.4 kg) dissolved in Ν,Ν-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t- butoxide (21.4 kg) and DMA (167.2 kg) at 20-25 °C. This mixture was then heated to 100- (0225) 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis ( (0226) 15 to 30 °C temperature . The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg) and finally with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6,7-dimethoxy-quinoline-4-yloxy)- phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6,7-dimethoxy- quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately lhour and then cooled to 0-5 °C and aged for approximately 1 h after which time the solid was filtered, washed with THF (147.6 kg) and dried on a filter under vacuum at approximately 25 °C to yield 4-(6,7-dimethoxyquinolin-3-yloxy)aniline (34.0 kg).
35 kg With sodium t-butanolate In N,N-dimethyl acetamide at 100 - 105℃; for 13 h; Large scale 10097] 4-Aminophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t-butoxide (21.4 kg) and DMA (167.2 kg) at 20-25° C. This mixture was then heated to 100-105° C. for approximately 13 hours. Afier the reaction was deemed complete as determined using in-process HPLC analysis (<2percent starting material remaining), the reactor contents were cooled at 15 to 20° C. and water (pre-cooled, 2 to 7° C., 587 L) charged at a rate to maintain 15 to 30° C. temperature. The resulting solid precipitate was filtered, washed with a mixture ofwater (47 L) and DMA (89.1 kg) and finally with water (214 L). The filter cake was then dried at approximately 25° C. on filter to yield crude 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75° C.) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately 1 h and then cooled to 0-5° C. and aged for approximately 1 h afier which time the solid was filtered, washed with THF (147.6kg) and dried on a filter undervacuum at approximately 25° C. to yield 4-(6,7-dimethoxy-quinoline-4-yloxy)- phenylamine (34.0 kg).
442 mg With sodium hydride In dimethyl sulfoxide at 20 - 100℃; for 3 h; At room temperature, will be 4-aminophenol (500 mg) is dissolved in dimethyl sulfoxide (DMSO) (5 ml), added and to 55percent sodium hydride (98 mg). Later, by adding 4-chloro -6,7-dimethoxy-quinoline (244 mg), and the mixture in 100 °C stirring 3 hours. The reaction solution is diluted with ethyl acetate, adding saturated aqueous solution of sodium bicarbonate, and stirring the mixture. Furthermore, by adding ethyl acetate and water, and extracting the organic layer. The organic layer with saturated aqueous salt solution washing, then drying with anhydrous sodium sulfate. The solvent is distilled under reduced pressure. The obtained residue is washed with methanol, to obtain the title compound (442 mg), which has the following physical property value.
34 kg at 100 - 105℃; for 13 h; Large scale In 20-25 °C lower, will be soluble in N, N-dimethyl acetic acid amine (DMA, 184.3 kg) in 4-amino phenol (24.4 kg) injected into the 4-chloro -6,7-dimethoxy-quinoline (35.3 kg), sodium butanol 3rd (21.4 kg), and DMA (167.2 kg) in the reactor. The mixture is then heated to 100-105 °C and heating for about 13 hours. HPLC analysis using in the process (less than 2percent residual starting material) determining after the reaction is complete, the contents of the reactor 15-20 °C lower cooling, and the water (pre-cool, 2 to 7 °C, 587 L) to a certain rate in order to maintain the temperature of injected 15-30°C. Filtering the resulting solid precipitate and water (47 L) and DMA (89.1 kg) washing and again a mixture of water (214 L) washing. Then on the filter and the filtration cake at about 25 °C lower drying, get the crude product 4 - (6,7-dimethoxy-quinolin-4-yloxy)- benzyl amine (to LOD computing, 59.4 kg of welded, 41.6 kg drymatter). The crude product 4 - (6,7-dimethoxy-quinolin-4-yloxy)- benzyl amine in tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) in the mixture (about 75 °C) about 1 hour, then cooling to 0-5°C, and aging about 1 hours, thereafter, filtering solid, to THF (147.6 kg) washing, on and in the filter, at a temperature of from about 25 °C the lower vacuum drying, to obtain 4 - (6,7-dimethoxy-quinolin-4-yloxy)- benzyl amine (34.0 kg).
34.0 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 13 h; Large scale Preparation of 4-(6, 7 -Dimethoxy-quinoline-4-yloxy)-phenylamine
4-Aminophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t-butoxide (21.4 kg) and DMA (167.2 kg) at 20-25 °C.
This mixture was then heated to 100-105 °C for approximately 13 hours.
After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining), the reactor contents were cooled at 15-20 °C and water (pre-cooled, 2-7 °C, 587 L) charged at a rate to maintain 15-30 °C temperature.
The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg) and finally with water (214 L).
The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7-dimethoxy-quinoline-4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7-dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately 1hour and then cooled to 0-5 °C and aged for approximately 1 hour after which time the solid was filtered, washed with THF (147.6 kg) and dried on a filter under vacuum at approximately 25 °C to yield 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylamine (34.0 kg).
208.3 g With sodium t-butanolate In N,N-dimethyl acetamide at 100 - 120℃; for 2 h; The 4-aminophenol 120g (1.1mol) was dissolved in 150ml (1.61mol) N, N- dimethyl acetamide at 20 ~ 25 , was slowly added to a solution of sodium tert-butoxide 171g (0.9mol) and 4- chloro-6,7-dimethoxy-quinolin-200g (0.9mol) in 400ml (4.30mol) N, N-dimethylacetamide was added dropwise after the reaction was heated to 100 ~ 120 , after two hours the remaining amount of starting material is detected by HPLC, and stopped when 2percent unreacted stop reaction, cooling to room temperature, poured into a 1L the ice water stirring 1 - 2 hours after the filtering, cake 200 ml water washing 2 times, and for 35 °C vacuum drying, yellowish-white powder from 4-(6,7dimethoxyquinolin-4-oxy)phenylamine 208.3g, molar yield 78.1percent
34.0 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 13 h; Large scale 4-Aminophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t-butoxide (21.4 kg), and DMA (167.2 kg) at 20—25 °C. This mixture was then heated to 100 — 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process 1-IPEC analysis (less than 2percent starting material remaining), the reactor contents were cooled at 15 to 20 °C, and water (pre-cooled, 2 to 7 °C, 587 L) was charged at a rate to maintain 15 to 30 °C temperature. The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg), and finally washed with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4—(6, 7 —dimethoxy—quinoline—4—yloxy)—phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4—(6, 7 —dimethoxy—quinoline—4—yloxy)— phenylamine was refluxed (approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately 1 hour, then cooled to 0 to 5 °C, and aged for approximately 1 hour, after which time the solid was filtered, washed with THF (147.6 kg), and dried on a filter under vacuum at approximately 25 °C to yield 4—(6, 7— dimethoxy—quinoline—4—yloxy)—phenylamine (34.0 kg).
34 kg With sodium t-butanolate In N,N-dimethyl acetamide at 20 - 105℃; for 0.13 h; Large scale [00168] 4-Aminophenol (24.4 kg) dissolved in N,N-dimethylacetamide (DMA, 184.3 kg) was charged to a reactor containing 4-chloro-6,7-dimethoxyquinoline (35.3 kg), sodium t- butoxide (21.4 kg), and DMA (167.2 kg) at 20 - 25 °C. This mixture was then heated to 100 - 105 °C for approximately 13 hours. After the reaction was deemed complete as determined using in-process HPLC analysis (less than 2percent starting material remaining), the reactor contents were cooled at 15 to 20 °C, and water (pre-cooled, 2 to 7 °C, 587 L) was charged at a rate to maintain 15 to 30 °C temperature . The resulting solid precipitate was filtered, washed with a mixture of water (47 L) and DMA (89.1 kg), and finally washed with water (214 L). The filter cake was then dried at approximately 25 °C on filter to yield crude 4-(6, 7 - dimethoxy-quinoline-4-yloxy)-phenylamine (59.4 kg wet, 41.6 kg dry calculated based on LOD). Crude 4-(6, 7 -dimethoxy-quinoline-4-yloxy)-phenylamine was refluxed(approximately 75 °C) in a mixture of tetrahydrofuran (THF, 211.4 kg) and DMA (108.8 kg) for approximately 1 hour, then cooled to 0 to 5 °C, and aged for approximately 1 hour, after which time the solid was filtered, washed with THF (147.6 kg), and dried on a filter under vacuum at approximately 25 °C to yield 4-(6, 7 -dimethoxy-quinoline-4-yloxy)- phenylamine (34.0 kg).

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[5] Patent: WO2013/166296, 2013, A1,
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YieldReaction ConditionsOperation in experiment
24 g
Stage #1: With potassium carbonate In tetrahydrofuran; water at 0 - 30℃; for 2 h;
Stage #2: at 25 - 75℃; for 1.16667 h;
Thionyl chloride (36.10 kgs) was slowly added to the mixture of l-((4-fluorophenyl) carbamoyl)cyclopropane carboxylic acid (22.60 kgs) and tetrahydrofuran (120 lts) at 25-30°C and stirred for 9 hours at the same temperature. The reaction mixture was slowly added to a pre-cool ed mixture of 4-((6,7-dimethoxyquinolin-4-yloxy)anil me (20.0 kgs), aqueous potassium carbonate solution (83.70 kgs of potassium carbonate in 120 Its of water) and tetrahydrofuran (120 Its) at 0-5°C. Raised the temperature of the reaction mixture to 25-30°C and stirred for 2 hours at the same temperature. Both the organic and aqueous layers were separated and water was added to the aqueous layer at 25-30°C. Extracted the aqueous layer with ethyl acetate. Combine the organic layers. Aqueous hydrochloric acid solution (15 lts of HC1 in 145 lts of water) was, added to the organic layer at 25-30°C and stirred the reaction mixture for 3 hours at the same temperature. Filtered the, precipitated solid, washed with tetrahydrofuran and ethyl acetate. To the obtained compound, water (lot-4) was added at 25- ‘30°C and stirred for •2 hours at the same temperature. Filtered the reaction mixture and washed with water. To the obtained compound, water (595 Its) and hydrochloric acid (1 .0 Its) were added at 25-30°C and stirred for.2 hours at the same temperature. Filtered the reaction mixture and washed with water. To the obtained compound, isopropanol (435 Its) was added at 25-30°C and stirred for 3 hours at the same temperature. Filtered the solid, washed with isopropanol and dried to get the title compound. Dimethyl sulfoxide (235 Its) was added to the obtained compound at 25-30°C and stirred for 45 ’iinutes at the same temperature. Filtercd the reaction mixture. Ethyl acetate (720 Its) was added to the obtained filtrate at 2 5-30°C and stirred for 3 hours at the same temperature. Filtered the precipitated solid, washed with ethyl acetate and dried to get the title compound.Yield: 32.99 kgs; Purity by HPLC: 99.8 5percent.
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