Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate
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Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate
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CAS No:
161798-02-3
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Formula:
C14H12N2O3S
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Chemical Name:
Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate
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Synonyms:
5-Thiazolecarboxylic acid,2-(3-cyano-4-hydroxyphenyl)-4-methyl-,ethyl ester;Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate;2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acid ethyl ester
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CAS No:
Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate Basic Attributes
288.32
288.32
1308068-626-2
DTXSID90694871
2934100090
Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate Use and Manufacturing
A solution of 1q (1.00 g, 3.4 mmol) and NH4OAc (0.54 g, 6.8 mmol) in ethanol (15 mL) was stirred for 30 min at 50 C. NaClO2 (80%, 0.62 g, 5.4 mmol) was then added and the mixture was stirred for 2h under nitrogen (TLC control, petroleum ether [boiling range:60-90 C)/EtOAc (3:1, v/v)]. After cooling, the filtrate was rotary evaporated to dryness and the residues were purified by column chromatography on silica gel (ethyl acetate/n-hexane, 1:8) to afford 2q' [yield 0.69 g (70%)]. Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate (2q?): Pale yellow solid; m.p. 184.5-185.5 C (lit.11 184.7-185.4 C);1H NMR (600 MHz, DMSO): delta 11.89 (s, 1H), 8.15 (d, J = 2.4 Hz, 1H), 8.05 (dd, J1 = 2.4 Hz, J2 = 4.2 Hz, 1H), 7.11-7.09 (m, 1H), 4.27 (q, J =7.2 Hz, 2H), 2.63 (s, 3H), 1.30 (t, J = 7.2 Hz, 3H); 13C NMR (150 MHz, DMSO): delta 167.5, 162.9, 161.7, 160.5, 133.3, 131.9, 124.3, 121.3, 117.4, 116.4, 100.3, 61.6, 17.6, 14.6; MS (ESI): 289.1 [M + H]+ (lit.11 MS (ESI):286.9 [M - H]-).To a solution of compound A (0.60 g, 2.08 mmol) in 15mL DMF was added K2CO3 (1.44 g, 10.41 mmol) and KI(0.17 g, 1.04 mol). After the mixture was activated at 80 Cfor 30 min, compound 7 (0.96 g, 6.24 mmol) was slowly added and maintained at 80 C for another 4 h. The mixturewas cooled to room temperature, treated with H2O (75 mL), and extracted with EtOAc (35 mL ). The combined organiclayers were washed with H2O (35 mL ) and brine, dried over anhydrous Na2SO4, filtered and evaporated todryness. The residue was crystalized in a mixture of EtOAc:hexane = 1: 2 to afford 8 (0.47 g, 63%) as yellow ctystals.8: mp 195-198 C, 1H NMR (400 MHz, CDCl3, ppm):1.13 (d, J = 6.8 Hz, 3H, CHCH3), 1.39 (t, 2H, J = 7.2 Hz, 3H, OCH2CH3), 1.85 (br, 1H, OH), 2.28 (m, 1H, CH), 2.78(s, 3H, ArCH3), 3.77 (m, 2H, HOCH2), 4.14 (m, 2H, ArOCH2), 4.36 (q, J = 7.2 Hz, 2H, COOCH2), 7.08 (d, J =8.8 Hz, 1H, ArH), 8.13 (dd, J = 2.4, 8.8 Hz 1H, ArH), 8.18(d, J = 2.4 Hz, 1H, ArH).A solution of compound A (0.50 g, 1.734 mmol), 2, 2-dimethyloxirane (1.25 g, 17.34 mmol), K2CO3 (0.24 g, 1.734mmol) and NaH2PO4 (0.21 g, 1.734 mmol) in CH3CN (40mL) and H2O (10 mL) was warned up to 150 C in a sealed tube for 12 h. Then the mixture was cooled to room temperature, diluted with H2O (60 mL) and extracted with EtOAc(30 mL ). The combined organic layers were washed with H2O (20 mL ) and brine (50 mL ), dried over anhydrous Na2SO4, filtered and evaporated to dryness. Flash chromatography on silica gel (petroleum ether/EtOAc) couldafford 9 (0.30 g, 48%) as colorless solid.9: mp 180-184 C, 1H NMR (400 MHz, CDCl3, ppm):1.42-1.37 (m, 9H, C(CH3)2 and CH2CH3), 2.78 (s, 3H, ArCH3), 3.97 (s, 2H, ArOCH2), 4.36 (q, J = 7.2 Hz, 2H, CH3CH2), 7.05 (d, J = 8.8 Hz, 1H, ArH), 8.14 (d, J = 8.8 Hz, 1H, ArH), 8.20 (s, 1H, ArH).
Febuxostat intermediate
Computed Properties
Molecular Weight:288.32
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:288.05686342
Monoisotopic Mass:288.05686342
Topological Polar Surface Area:111
Heavy Atom Count:20
Complexity:409
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazolecarboxylate
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