* 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.
Reference：
[1] Journal of the Chemical Society, 1945, p. 622,625
2
[ 49679-45-0 ]
[ 1448-87-9 ]
Reference：
[1] Journal of the Chemical Society, 1945, p. 622,625
3
[ 49679-45-0 ]
[ 20254-76-6 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1253 - 1256
[2] Archiv der Pharmazie, 2012, vol. 345, # 9, p. 687 - 694
[3] Journal of the Chemical Society, 1945, p. 622,625
[4] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 161,163; engl. Ausg. S. 145, 147
[5] Journal of the Chemical Society, 1945, p. 622,625
[6] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 5, p. 1139 - 1143
4
[ 36818-07-2 ]
[ 49679-45-0 ]
Yield
Reaction Conditions
Operation in experiment
100%
at 0℃; for 0.5 h; Reflux
Into a dry three-neck round bottom flask was introduced compound 2 (218 mg, 1.00 mmol) in phosphorous oxychloride (2 mL) at ice bath temperature. Dimethylformamide (0.1 mL) was then added at 0 C and the reaction mixture was refluxed for 30 min. After cooling, the resulting mixture was diluted with ethyl acetate and washed with a 10percent sodium hydroxide solution (2 5 mL), and brine (2 10 mL). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure to obtain derivative 3 (237 mg, 100percent) as a beige solid. Mp 46.4 C. 1 H NMR (300 MHz, CDCl3) d 8.18 (m, 1H), 8.07 (m, 1H), 7.92e7.81 (m, 2H), 4.58 (q, 2H, J 7.2 Hz, CH2), 1.49 (t, 3H, J 7.2 Hz, CH3). 13C NMR (75 MHz, CDCl3) d 163.9, 144.7, 143.9, 142.2, 139.7, 132.6, 131.0, 129.6, 128.3, 63.0, 14.1.
Reference：
[1] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 101 - 109
[2] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 5, p. 1139 - 1143
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1253 - 1256
[4] Journal of the Chemical Society, 1945, p. 622,625
[5] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 161,163; engl. Ausg. S. 145, 147
[6] Archiv der Pharmazie, 2012, vol. 345, # 9, p. 687 - 694
[7] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 6, p. 1721 - 1737
5
[ 36818-07-2 ]
[ 49679-45-0 ]
Yield
Reaction Conditions
Operation in experiment
77%
Stage #1: at 115℃; for 0.166667 h; Stage #2: at 0℃;
Step F (Compound 6) [00140] A mixture of compound 5 (4.5 g. /20.6 mmol) and Phosphorous oxychloride was heated to 115 degrees for ten minutes. The excess phosphorous oxychloride was removed at reduced pressure and the residue was poured onto two hundred fifty grams of crushed ice. The mixture was neutralized by the addition of ammonium hydroxide and then extracted with ethyl ether. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness. No further purification, material used as is. Yield: 3.74 g. approximately 77percent. IH NMR (500 MHz, CDC13) 8 8.22 (d, 1H), 8. 11 (d, 1H), 7.95-7. 86 (m, 2H), 4.60 (q, 2H), 1.50 (t, 3H).
Reference：
[1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 1013 - 1024
[2] Patent: WO2005/56547, 2005, A2, . Location in patent: Page/Page column 43
[3] Journal of the Indian Chemical Society, 1986, vol. 63, p. 427 - 429
6
[ 609-09-6 ]
[ 49679-45-0 ]
Reference：
[1] Journal of the Indian Chemical Society, 1986, vol. 63, p. 427 - 429
[2] Journal of the Chemical Society, 1945, p. 622,625
[3] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 101 - 109
7
[ 95-54-5 ]
[ 49679-45-0 ]
Reference：
[1] Journal of the Chemical Society, 1945, p. 622,625
[2] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 101 - 109
8
[ 95-54-5 ]
[ 609-09-6 ]
[ 49679-45-0 ]
Reference：
[1] Archiv der Pharmazie, 2012, vol. 345, # 9, p. 687 - 694
9
[ 23395-75-7 ]
[ 49679-45-0 ]
Reference：
[1] Journal of the Chemical Society, 1945, p. 622,625
[2] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 161,163; engl. Ausg. S. 145, 147
10
[ 7065-23-8 ]
[ 49679-45-0 ]
Reference：
[1] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 161,163; engl. Ausg. S. 145, 147
A solution of <strong>[49679-45-0]ethyl <strong>[49679-45-0]3-chloroquinoxaline-2-carboxylate</strong></strong> (500 mg, 2.12 mmol) in morpholine (5 mL was stirred for 1 hour at 100 C. It was diluted with water, extracted with EA (x3), washed with brine (x2). The organic layer was dried and concentrated to give 450 mg (cmde) of desired compound as yellow oil, which was used directly in the next step without further purification. ESI MS m/z = 287.5 [M+Hjt
at 100℃; for 1h;
A solution of <strong>[49679-45-0]ethyl <strong>[49679-45-0]3-chloroquinoxaline-2-carboxylate</strong></strong> (500 mg, 2.12 mmol) in morpholine (5 mL was stirred for 1 hour at 100C. It was diluted with water, extracted with EA (x3), washed with brine (x2). The organic layer was dried and concentrated to give 450 mg (crude) of desired compound as yellow oil, which was used directly in the next step without further purification. ESI MS m/z = 287.5 [M+H]+.
(S)-2-[(3-{4-[((S)-1,3-Bis-ethoxycarbonyl-propylcarbamoyl)-methyl]-phenylamino}-quinoxaline-2-carbonyl)-amino]-pentanedioic acid diethyl ester[ No CAS ]
EXAMPLE 14 2-[(1-Methylethylamino)(1-methylethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride 2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (4.73 g., 0.02 mole) and 3.206 g. (0.02 mole) of <strong>[2986-17-6]1,3-diisopropylthiourea</strong> were dissolved in 90 ml. of acetone and 10 ml. of acetic acid. The solution was heated on the steambath for 23/4 hours and filtered hot. The solvent in the filtrate was evaporated and the residue was triturated with ether until it solidified. Filtration gave 2.33 g. of crude product. Recrystallized from acetone-ether it afforded 1.28 g. (16.1percent) of a yellow solid, m.p. 148°-149° C. (dec). Analysis for: C18 H25 ClN4 O2 S Calculated: C, 54.47; H, 6.35; N, 14.12; Cl, 8.93; S, 8.08. Found: C, 54.44; H, 6.18; N, 14.19; Cl, 8.96; S, 8.25.
EXAMPLE 2 Preparation of 5-(3-(4-fluoro-2-methoxyphenoxy)quinoxaline-2-carboxamido)picolinic [00621] A mixture of ethyl 3-chloroquinoxaline-2-carboxylate (300 mg, 1.27 mmol), 4-fluoro- 2-methoxy-phenol (289.0 mu, 2.54 mmol) and Cs2C03 (826.3 mg, 2.54 mmol) in NMP (3.0 mL) was stirred at 100 C for 3 hours. The reaction mixture was poured into water, the pH was adjusted to pH 6 with IN HCl and the mixture was extracted with ethyl acetate (3x). The organics were combined, washed with brine, dried over Na2S04 and evaporated to dryness. Purification by column chromatography using a gradient of MeOH in dichloromethane (0 -10%) gave 3-(4-fluoro-2-methoxy- phenoxy)quinoxaline-2-carboxylic acid (360 mg, 90%) as a red oil. ESI-MS m/z calc. 314.07, found 315.1 (M+l)+; Retention time: 1.35 minutes (3 minutes run).
ethyl 3-((3-morpholinophenyl)amino)quinoxaline-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
With toluene-4-sulfonic acid; In ethanol; for 110h;Reflux;
General procedure: Method A: a solution of compound 3 (1.11 g, 4.70 mmol), 3- aminophenol (622 mg, 5.70 mmol) and p-TSA, as a catalyst, in absolute ethanol (40 mL) was refluxed for 110 h. Ethanol was then evaporated under reduced pressure, and the resulting residue was purified by silica column chromatography using cyclohexane with ethyl acetate gradient (0e50%) as eluent to give the desired compound 4a (1.0 g, 69%) as a red powder.
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