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Chemical Structure| 179688-29-0
Chemical Structure| 179688-29-0
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Product Details of [ 179688-29-0 ]

CAS No. :179688-29-0 MDL No. :MFCD02678087
Formula : C14H18N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :PMQWTUWLIGJTQD-UHFFFAOYSA-N
M.W : 294.30 Pubchem ID :135409305
Synonyms :
Chemical Name :6,7-Bis(2-methoxyethoxy)quinazolin-4(3H)-one

Calculated chemistry of [ 179688-29-0 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.43
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.75
TPSA : 82.67 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 0.35
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 0.1
Log Po/w (SILICOS-IT) : 2.59
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.71
Solubility : 5.74 mg/ml ; 0.0195 mol/l
Class : Very soluble
Log S (Ali) : -1.65
Solubility : 6.58 mg/ml ; 0.0224 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.58
Solubility : 0.00769 mg/ml ; 0.0000261 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.54

Safety of [ 179688-29-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 179688-29-0 ]

* 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 [ 179688-29-0 ]
  • Downstream synthetic route of [ 179688-29-0 ]

[ 179688-29-0 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 1208902-93-5 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
93% With peracetic acid; sulfuric acid In ethanol at 60℃; for 4 h; General procedure: To a solution of 6,7-dimethoxyquinazoline 1a (200.0 mg, 1.05 mmol) in ethanol (20 mL) were added 40percent peracetic acid (1.0mL, 5.26 mmol) and 0.01 mL sulfuric acid (1.8 mmol). After the reaction was stirred at 60°C for 4–12 h (see Table 2) and then cooled to room temperature, excess sodium bisulfite (541.8 mg, 5.26 mmol) was added to get rid of the peroxide. The solid was filtered off after stirring for 20 min, and the filtrate was concentrated under reduced pressure to give the crude product, which was washed by ethanol and petroleum ether to give 2a as a light yellow solid (179.7 mg, 83percent), mp>300°C.
Reference: [1] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
[2] Tetrahedron, 2010, vol. 66, # 4, p. 962 - 968
  • 2
  • [ 179688-27-8 ]
  • [ 149-73-5 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
91% With ammonium acetate In methanol at 110℃; for 6 h; In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.02 g (3.3 mmol) of ethyl 4,5-bis(2-methoxyethoxy)anthranilate, 0.96 g (9.1 mmol) of methyl orthoformate, 0.69 g (9.1 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 110°C for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Then, the concentrate was recrystallized from 20 mL of methanol. The crystalline product was collected by filtration and dried under reduced pressure to give 0.87 g (isolated yield: 91percent) of 6,7-bis(2-methoxyethoxy)quinazolin-4-one as a white crystalline product.
91% With ammonium acetate In methanol at 60 - 70℃; for 7 h; [Synthesis Example 4]; (Synthesis of 6,7-bis(2-methoxyethoxy)quinazolin-4-one); In a 20 L-volume glass reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 1,600 g (5.11 moles) of the ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate prepared in the Synthesis Example 3, 1,626 g (15.3 moles) of methyl orthoformate, 1,181 g (15.3 moles) of ammonium acetate and 4,800 mL of methanol were placed. The mixture was allowed to react under refluxing conditions (60 to 70°C) for 7 hours while stirring. After the reaction was complete, the reaction solution was cooled to 60°C. To the reaction solution, 4,800 mL of methanol was added. The mixture was stirred for 30 minutes while maintaining the temperature, cooled to 0 to 5°C, and further stirred for 1 hour. The resulting mixture was filtered to obtain 1,373 g of 6,7-bis(2-methoxyethoxy)quinazolin-4-one as white crystals (isolation yield: 91percent).
Reference: [1] Patent: EP1477481, 2004, A1, . Location in patent: Page 20
[2] Patent: EP1650196, 2006, A1, . Location in patent: Page/Page column 7
  • 3
  • [ 149-73-5 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
83% With ammonium acetate In methanol at 95℃; for 8 h; In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.00 g (2.8 mmol) of 4,5-bis(2-methoxyethoxy)anthranilic acid, 0.93 g (8.8 mmol) of methyl orthoformate, 0.67 g (8.8 mmol) of ammonium acetate, and 5.0 mL of methanol. The reaction was carried out at 95°C for 8 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Then, the concentrate was recrystallized from 20 mL of methanol. The crystalline product was collected by filtration and dried under reduced pressure to give 0.85 g (isolated yield: 83percent) of 6,7-bis(2-methoxyethoxy)quinazolin-4-one as a white crystalline product. 6,7-Bis(2-methoxyethoxy)quinazolin-4-one had the following characteristics. 1H-NMR (D2O, δ (ppm)): 3.49 (3H, s), 3.50 (3H, s), 3.86-3.88 (4H, m), 3.97 (2H, d, J=3.6Hz), 4.04 (2H, d, J=3.6Hz), 6.41 (1H, s), 6.72 (1H, s), 7.72 (1H, s) CI-MS (m/e): 295 (M+1)
Reference: [1] Patent: EP1477481, 2004, A1, . Location in patent: Page 19
  • 4
  • [ 3473-63-0 ]
  • [ 179688-27-8 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: at 80℃; for 5 h; Inert atmosphere
Stage #2: for 1 h; Reflux
Compound (v) (171.1g), formamidine acetate (79.8 g) was dissolved in n-butanol (1027mL), and nitrogen at elevatedTemperature to 80 ° C for 5 hours, the reaction was complete by HPLC. Spin dry n-butanol, was added 1711g of isopropyl acetate heated to reflux for 1Hours, cooled to _5 ° C for 4 hours. Filtered, 50 ° C and dried under blast (vi) (164.0g), yield 98percent, purity>95percent. NMR data identified compound (vi) as follows
98.5% at 55℃; for 3 h; Green chemistry 2375 ml of absolute ethanol and 255 g of compound III prepared by the method of Example 9 were added to the reaction vessel,After stirring to dissolve, add formamidine acetate 95g, heated to 55°C , temperature control reaction for 3 hours, cooled to 15 crystal out. Filtration, the filtrate evaporated condensate recovery of ethanol applied to the next batch of ring reactor, non-condensable gas into the exhaust absorption device. The filter cake was collected and dried at 40-50 ° C,The structure was confirmed to give the finished product 6,7-bis (methoxyethoxy) quinazolin-4-one 235.7g, the yield was 98.5percent, by HPLC purity of 99.9percent.
Reference: [1] Patent: CN103709110, 2016, B, . Location in patent: Paragraph 0067; 0068
[2] Patent: CN107382880, 2017, A, . Location in patent: Paragraph 0029-0041
[3] European Journal of Medicinal Chemistry, 2008, vol. 43, # 7, p. 1478 - 1488
  • 5
  • [ 67-56-1 ]
  • [ 236750-62-2 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
85% at 130℃; Microwave irradiation; Inert atmosphere 2-amino-4,5-bis(2-methoxyethoxy)benzamide (284 mg, 1 mmol),[Cp*Ir(2,2'-bpyO)(H2O)] (10.8 mg, 0.01 mmol,1 molpercent), cesium carbonate (98 mg, 0.3 mmol, 0.3 equiv.)Add methanol (0.5 mL) to dry 5 mL Microwave reaction tube.Microwave tube nitrogen protection,Placed in a single mode pressure microwave synthesizer (Discover CEM, USA).The reaction mixture reacts at 130 oC for 2 hours.Cool to room temperature.Rotary evaporation removes the solvent,Then through column chromatography(Developer: petroleum ether/ethyl acetate)Pure target compound obtained, yield: 85percent
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2580 - 2583
[2] Patent: CN107337648, 2017, A, . Location in patent: Paragraph 0011; 0014
  • 6
  • [ 107-31-3 ]
  • [ 476168-17-9 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
92% With ammonia In methanol for 7 h; Reflux in 2000 ml three-mouth bottle, by adding 200g (1eq) ELTF, 246g (4eq) the methyl formate, 182g (4eq) and ammonium 600 ml methanol, reflux stirring for 7 hours. After the reaction is complete, the reaction solution is cooled to 60 °C. In the reaction solution is added to 600 ml methanol. Preserving heat and stirring 30 minutes, cooling to 5 °C, stirring 1 hour. Filtering the resulting mixture, was 173.5g ELTG white solid, yield = 92percent.
Reference: [1] Patent: CN105566233, 2016, A, . Location in patent: Paragraph 0015; 0057
  • 7
  • [ 50-00-0 ]
  • [ 236750-62-2 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
92% at 130℃; for 24 h; 2-Amino-4,5-bis[(2-methoxy)-ethoxy]-benzamide (cas:236750-62-2, 2.84 g, 10 mmol)A mixture of paraformaldehyde (600 mg, 20 mmol monomer) [monomer molar ratio: 1:2] was added to the reaction flask,Then 10 ml of water was added, and the temperature was raised to 130 degrees by sealing. The reaction was allowed to proceed for 24 hours and then allowed to stand. The solid was filtered off and recrystallized from ethyl acetate.This gave 6,7-bis[(2-methoxy)-ethoxy]-quinazolin-4-one 2.70 g in 92percent yield.
Reference: [1] Patent: CN107445907, 2017, A, . Location in patent: Paragraph 0022; 0023; 0028-0056; 0059; 0060; 0062-0065
  • 8
  • [ 77287-34-4 ]
  • [ 179688-27-8 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
72% at 165 - 170℃; for 12 h; Inert atmosphere 1.8 Synthesis of 6,7-bis(methoxyethoxy)quinazolin-4-one
0.18 mol ethyl 6-amino-3,4-bis(methoxyethoxy)benzoate was dissolved in 50 ml formamide, under N 2 protection at 165-170 °C for 12h. After cooling solid precipitate was filtered. The resulting solid was recrystallized from acetonitrile to give white solid. Yield 72percent.
Reference: [1] Molecules, 2006, vol. 11, # 4, p. 286 - 297
[2] Patent: CN103193722, 2016, B, . Location in patent: Paragraph 0115; 0116; 0117
[3] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 293 - 301
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 42 - 53
  • 9
  • [ 77287-34-4 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
81% at 160℃; Large scale To a 1 L reaction flask was added 200 g of ethyl 2-amino-4,5-dimethoxyethoxybenzoate hydrochloride, Formamide 300 ml, formic acid 60 ml. Heated to 160 ° C reaction, TLC monitored the reaction until the starting material disappeared. After completion of the reaction, the mixture was cooled to room temperature, Put in the refrigerator to cool overnight, The filter cake was washed with acetone and air dried for 5 h. To obtain a white solid compound (1,134.6 g) in a yield of 81percent
Reference: [1] Patent: CN103980207, 2016, B, . Location in patent: Paragraph 0039-0040
  • 10
  • [ 16712-16-6 ]
  • [ 77287-34-4 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
80% at 25 - 145℃; Ethyl-2-amino-4, 5-bis (2-methoxy ethoxy) benzoate (bOg; 0285 mol) obtained by the process cited in Example No.1, was charged with formamide (226.8 g; 5.035 mol) and animonium formate (1 8g) at a temperature about 25-35°C.The temperature of the reactionmass was raised to 140-145°C. After the completion of reaction, water was added (200 mL) followed by stirring with methylene chloride (l000mL). The organic fractions was isolated and distilled out at a temperature about 40-45°C. The residue was treated with ethyl acetate filtered and suck dried. The resultant compound was dried under vacuum to obtain the title compound (80g; yield: 80percent).
Reference: [1] Patent: WO2013/156835, 2013, A1, . Location in patent: Page/Page column 12; 13
  • 11
  • [ 3943-89-3 ]
  • [ 179688-29-0 ]
Reference: [1] Molecules, 2006, vol. 11, # 4, p. 286 - 297
[2] Molecules, 2006, vol. 11, # 4, p. 286 - 297
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 829 - 843
[4] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 293 - 301
[5] Chemistry - A European Journal, 2015, vol. 21, # 41, p. 14342 - 14346
[6] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 42 - 53
  • 12
  • [ 183322-16-9 ]
  • [ 179688-29-0 ]
Reference: [1] Molecules, 2006, vol. 11, # 4, p. 286 - 297
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 829 - 843
[3] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 293 - 301
[4] Chemistry - A European Journal, 2015, vol. 21, # 41, p. 14342 - 14346
[5] Patent: CN103193722, 2016, B,
[6] Patent: CN103709110, 2016, B,
[7] Patent: CN107382880, 2017, A,
[8] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 42 - 53
  • 13
  • [ 179688-26-7 ]
  • [ 179688-29-0 ]
Reference: [1] Molecules, 2006, vol. 11, # 4, p. 286 - 297
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 829 - 843
[3] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 293 - 301
[4] Patent: WO2013/156835, 2013, A1,
[5] Patent: CN103193722, 2016, B,
[6] Patent: CN103709110, 2016, B,
[7] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 42 - 53
  • 14
  • [ 236750-65-5 ]
  • [ 64-18-6 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
  • 15
  • [ 236750-62-2 ]
  • [ 122-51-0 ]
  • [ 179688-29-0 ]
YieldReaction ConditionsOperation in experiment
158 g With trifluoroacetic acid In ethyl acetate for 4 h; Reflux 61 g of the compound II (2-amino-4,5-bis (2-methoxyethoxy) benzamide)106.3 g of triethyl orthoformate and 7 g of trifluoroacetic acid were added to about 1.7 L of ethyl acetate and heated to reflux for about 4 h. TLC was monitored until the reaction was complete and the reaction was stopped. The reaction solution was cooled to room temperature, a large amount of solid was precipitated,The solid was collected and dried in vacuo to give 158 g of compound III solid,The purity was determined by HPLC with a purity of 99percent and a yield of 90percent.
Reference: [1] Patent: CN104945332, 2017, B, . Location in patent: Paragraph 0030-0031; 0035-0036
  • 16
  • [ 54060-30-9 ]
  • [ 183322-18-1 ]
  • [ 179688-29-0 ]
  • [ 183319-69-9 ]
Reference: [1] Patent: WO2011/76813, 2011, A1, . Location in patent: Page/Page column 19
[2] Patent: EP2348020, 2011, A1, . Location in patent: Page/Page column 11
  • 17
  • [ 16712-16-6 ]
  • [ 179688-27-8 ]
  • [ 179688-29-0 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 829 - 843
  • 18
  • [ 80407-64-3 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
[3] Patent: CN105566233, 2016, A,
[4] Patent: CN107445907, 2017, A,
  • 19
  • [ 819813-71-3 ]
  • [ 179688-29-0 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 41, p. 14342 - 14346
[2] Patent: CN103193722, 2016, B,
[3] Patent: CN105566233, 2016, A,
  • 20
  • [ 80407-68-7 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Patent: CN107445907, 2017, A,
  • 21
  • [ 139-85-5 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Patent: CN105566233, 2016, A,
  • 22
  • [ 179688-14-3 ]
  • [ 179688-29-0 ]
Reference: [1] Medicinal Chemistry, 2011, vol. 7, # 4, p. 295 - 300
[2] Patent: CN105566233, 2016, A,
  • 23
  • [ 236750-65-5 ]
  • [ 179688-29-0 ]
Reference: [1] Patent: CN104945332, 2017, B,
[2] Patent: CN107445907, 2017, A,
  • 24
  • [ 1006377-63-4 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
  • 25
  • [ 501684-22-6 ]
  • [ 179688-29-0 ]
Reference: [1] Medicinal Chemistry, 2011, vol. 7, # 4, p. 295 - 300
  • 26
  • [ 1384975-87-4 ]
  • [ 179688-29-0 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 3, p. 346 - 351
  • 27
  • [ 121-33-5 ]
  • [ 179688-29-0 ]
Reference: [1] Patent: CN105566233, 2016, A,
  • 28
  • [ 1172625-04-5 ]
  • [ 179688-29-0 ]
Reference: [1] Patent: CN107445907, 2017, A,
  • 29
  • [ 3473-63-0 ]
  • [ 476168-17-9 ]
  • [ 179688-29-0 ]
Reference: [1] Patent: WO2006/84882, 2006, A2, . Location in patent: Page/Page column 12
[2] Medicinal Chemistry, 2011, vol. 7, # 4, p. 295 - 300
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