Heterocyclic Building Blocks-Thiazole

533-30-2, 6-Aminobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

533-30-2, Example B22 To a stirring suspension of 6-aminobenzothiazole (0.500 g, 3.33 mmol) in cone. HCl (5 ml) at 0-5 C. was added a solution of NaNO2 (0.276 g, 3.99 mmol) in H2O (5 ml). The mixture was stirred at 0-5 C. for 75 min until a clear yellow solution was obtained. To this was then added a solution of SnCl2.2H2O (2.76 g, 13.3 mmol) in conc. HCl (5 ml). After completing the addition, the suspension was stirred at RT for 2 h. 4-Methyl-3-oxopentanenitrile (0.444 g, 3.99 mmol) and EtOH (50 ml) were added and the reaction was stirred with heating at 75 C. After 18 h, the completed reaction was cooled to RT and concentrated to an aqueous residue. This was chilled thoroughly in ice and made strongly basic (pH 12-13) by the addition of 6M NaOH. While still cold the mixture was extracted with EtOAc (2*). The combined organics were washed with H2O (2*), brine (1*), dried (MgSO4), filtered and evaporated to afford crude 1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-amine (0.8 g, 93% yield) as an oil which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6) delta 9.36 (s, 1H), 8.30 (d, J=2.4 Hz, 1H); 8.10 (d, J=8.8 Hz, 1H), 7.74 (dd, J=2.4 and 8.8 Hz, 1H), 5.36 (s, 1H), 5.33 (brs, 2H), 2.76 (septet, J=6.8 Hz, 1H), 1.17 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 259.0 (M+H+).

As the paragraph descriping shows that 533-30-2 is playing an increasingly important role.

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; US2008/90856; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.38205-60-6,1-(2,4-Dimethylthiazol-5-yl)ethanone,as a common compound, the synthetic route is as follows.

Example 111-[N,N-dimethylaminocarbonyl-methyl]-2-[2-(2,4-dimethylthiazol-5-yl)-quinolin- 6-yl]-3-cyclohexyl-1H-indole-6-carboxylic acid (Compound 212) Preparation of 6-bromo-2-(2,4-dimethyl-thiazol-5-yl)-quinoline (125): [0217] A mixture of 1.071 g (5.354 mmol) compound 110, 723 muL (5.354 mmol) 5- acety1-2,4-dimethylthiazole and 9.0 mL 10% KOH/ethanol (16.062 mmol KOH) in 60 mL ethanol was refluxed overnight under argon. It was then evaporated and the residue triturated with water. The solid crude product was filtered through a 250 mL silica pad using a 10% to 60% toluene-ethylacetate gradient to give 1.164g (68%) compound 125,1H-NMR (DMSO-d6): delta(ppm) 8.39 (d, 1H, J=8.7Hz), 8.27 (m, 1H), 7.88-7.86 (m, 3H), 2.68 (s, 3H), 2.64 (s, 3H).; Example 88 Step 1. 6-Bromo-2-(2,4-dimethyl-thiazol-5-y1)-quinoline (125)[0307] To a solution of KOH (10.32 (85%) g, 156.27 mmol) in anhydrous EtOH (700 mL) was added 2-amino-5-bromobenzaldehyde (10.42 g, 52.09 mmol) and 5-acety1- 2,4-dimethylthiazole (8.16 mL, 60.42 mmol). The mixture was stirred under Ar at 78 0C for 16 h and then cooled down in an ice-bath. It was neutralized to pH 7 with 5 N HCl and then evaporated to about 60 mL. Water (500 mL) was added. The precipitate formed were collected by filtration, washed thoroughly with water, and dried to give 125 (15.62 g, 94%).

38205-60-6, The synthetic route of 38205-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENELABS TECHNOLOGIES, INC.; WO2006/76529; (2006); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

80945-86-4,80945-86-4, 6-Bromo-2-chlorobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

One equivalent of 6-bromo-2-chlorobenzo[d]thiazole and 1.1 equivalents of (R)-1-(pyrrolidin-3-yl)piperidine (freebase of Reference Example 5C) are weighed into a 10 mL CEM microwave vial equipped with a magnetic stirbar. N,N-Dimethylformamide or 2-methoxyethanol is added to give approximately a 2 M solution followed by four equivalents of N,N-diisopropylethylamine. The reaction mixture was heated to 150 C. under microwave irradiation with the cooling power on for 20 minutes. The reaction mixture volatiles are then removed under reduced pressure. The residue is partitioned between saturated aqueous sodium carbonate and CHCl3. The aqueous layer is extracted once more with CHCl3, then the combined organic extracts are washed with brine, dried (MgSO4), and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel, eluting with 97:3 dichloromethane/2 M ammonia in methanol. Fractions containing product are combined and concentrated under reduced pressure to give a solid that is dissolved in hot ethyl acetate, dried (MgSO4), and filtered. The filtrate is concentrated under reduced pressure to give (R)-6-methoxy-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole.

As the paragraph descriping shows that 80945-86-4 is playing an increasingly important role.

Reference£º
Patent; Abbott Laboratories; US2009/163464; (2009); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6436-59-5,Ethyl 2-methylthiazole-4-carboxylate,as a common compound, the synthetic route is as follows.

6436-59-5, A solution of 2-methyl-thiazole-4-carboxylic acid ethyl ester (1.26g, 7.36 mmol) in ethyl ether (10 mL) was cooled to -78 C and treated with a solution of LAH (0.83g, 21.9 mmol) in dry THF (30 mL) added dropwise over 10 min. After 3 hours, at -78 C, the mixture was quenched with sat. Na2S04 (app. 20 mL). The mixture was allowed to warm up to 22 C and was extracted with ethyl ether (4 x 50 mL). The combined extracts were washed with brine, dried over anhydrous MgS04 and concentrated to give an oil. Filtration on a silica gel pad (3 x 7 cm) and elution with ethyl acetate gave an oil which was distilled to afford the title material (0.664g, 70%) as an oil which crystallized. B.p. 60-70 C / 0.2 torr. HRMS(ESI) calcd for C5H8NOS [M+H]+ m/z 130.0321, found 130.0342. 1H NMR (CDCl3, 600 MHz) delta 6.99 (d, J= 0.8 Hz, 1H), 4.70 (s, 1H), 2.98 (br s, 1H), 2.68 (s, 3H).

The synthetic route of 6436-59-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; BANVILLE, Jacques; REMILLARD, Roger; RUEDIGER, Edward H.; DEON, Daniel H.; GAGNON, Marc; DUBE, Laurence; GUY, Julia; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; MAXWELL, Brad D.; WONG, Pancras C.; WO2013/163279; (2013); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61830-23-7,Ethyl 5-bromothiazole-4-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of ethyl 5-bromothiazole-4-carboxylate (3.49 g, 14.77 mmol, 0.9 eq), tert-butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (5.70 g, 16.41 mmol, 1 eq), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (120 mg, 0.16 mmol, 0.01 eq), potassium carbonate (4.54 g, 32.83 mmol, 2 eq) in mixture of dioxane (130 mL) and water (22 mL) was degassed and purged with nitrogen for three times, and then the mixture was stirred at 80 C. for 10 hours under nitrogen atmosphere. The reaction mixture was concentrated and added water (50 mL), then extracted with ethyl acetate (60 mL) two times. The combined organic layers were washed with saturated aqueous sodium chloride (50 mL) two times, dried over anhydrous sodium sulfate, concentrated to give crude product. The crude product was purified by silica gel chromatography (petroleum ether:ethyl acetate=1:0 to 1:1). Compound ethyl 5-[4-[(1S)-1-(tert-butoxycarbonylamino)ethyl]phenyl]thiazole-4-carboxylate (5.07 g, 13.48 mmol, 82% yield) was obtained as a yellow solid.

61830-23-7, 61830-23-7 Ethyl 5-bromothiazole-4-carboxylate 12361218, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; Arvinas Operations, Inc.; Genentech, Inc.; Crew, Andrew P.; Wang, Jing; Berlin, Michael; Dragovich, Peter; Chen, Huifen; Staben, Leanna; US2019/300521; (2019); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

2933-29-1, 2-Amino-4,5,6,7-tetrahydrobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 134 S-5-Fluoro-1H-indole-2-carboxylic acid [2-phenyl-1-(4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl)-ethyl]-amide From S-2-[(5-fluoro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid and 4,5,6,7-tetrahydro-benzothiazol-2-yl-amine. mp 162 – 165 C.

2933-29-1, 2933-29-1 2-Amino-4,5,6,7-tetrahydrobenzothiazole 18046, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; EP1134213; (2001); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.155559-81-2,5-Fluorobenzo[d]thiazole-2-thiol,as a common compound, the synthetic route is as follows.

Example 40Preparation of7V,7V-dicyclopropyl-6-ethyl-4-(5-fluorobenzo[d]thiazol-2-ylamino)-l- methyl-l,6-dihydroimidazo [4,5-d] pyrrolo [2,3-b] pyridine-7-carboxamide 40A Preparation of 5-fluoro-2- methylthio)benzo|”d”lthiazole[00284] To a solution of 5-fluoro-2-mercaptobenzothiazole (0.15 g, 0.810 mmol) in THF (8.10 niL) cooled to 0 C was added sodium hydride (0.036 g, 0.891 mmol). After stirring 10 min, iodomethane (0.076 mL, 1.215 mmol) was added and the reaction mixture was slowly warmed to room temperature over 2 h. The reaction was diluted with ethyl acetate and quenched with saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. 5-fluoro-2-(methylthio)benzo[d]thiazole (0.178 g, 110 % yield) was isolated as a white solid. Material was used without any further purification.[00285] MS (ESI) m/z 200.0 (M+H)[00286] 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 7.68 (dd, 1H, J= 8.81, 5.04 Hz), 7.56 (dd, 1H, J= 9.57, 2.52 Hz), 7.07 (td, 1H, J= 8.81, 2.52 Hz), 2.80 (s, 3H), 155559-81-2

The synthetic route of 155559-81-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

19759-66-1, 2-Aminobenzothiazole-6-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of benzofurane-2-carbonyl chloride 1 in dry toluene, a solution of corresponding anilines and amino-pyridines 2a-j, 2-aminobenzothiazoles 4a, 4c and 5a and 2-aminobenzimidazoles 4b, 4d and 5b in dry toluene was added dropwise, followed by the addition of Et3N. The mixture was refluxed for several hours. After cooling, the resulting products were filtered off and recrystallized from methanol to obtain benzofurane-2-carboxamides 3a, 3b, 3d-j and 6a-f., 19759-66-1

As the paragraph descriping shows that 19759-66-1 is playing an increasingly important role.

Reference£º
Article; Hranjec, Marijana; Sovic, Irena; Ratkaj, Ivana; Pavlovic, Gordana; Ilic, Natasa; Valjalo, Linda; Pavelic, Kresimir; Kraljevic Pavelic, Sandra; Karminski-Zamola, Grace; European Journal of Medicinal Chemistry; vol. 59; (2013); p. 111 – 119;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.161798-01-2,Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate,as a common compound, the synthetic route is as follows.

A solution of compound NL (1.03mmol, 300mg, obtained from the method previously reported) [16] in 9 CH2Cl2 (20mL) and 10 Et3N (0.5mL) were added to a round-bottom flask. The mixture was stirred in an ice-water bath. A solution of 11 2,4-dinitrobenzene sulfonyl chloride (1.24mmol, 330mg) in CH2Cl2 (10mL) was added to the mixture dropwise over 0.5h. The mixture was stirred at 0¡ãC for 1h. The mixture then continued to be stirred at room temperature for 2h until thin layer chromatography indicated the reaction was complete. The organic phase was washed with 60mL of 12 water (3¡Á20mL) and then dried over MgSO4. The solvent was concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (eluted with hexanes to 13 ethyl acetate: hexane=1:4) to afford a yellow solid of 14 NL-S in 36.9percent yield (197mg, 0.38mmol). Melting point: 185.4?186.0¡ãC. 1H NMR (600MHz, DMSO?d6): delta 10.12 (s, 1H, -CHO), 9.12 (d, J=2.4Hz, 1H, ph-H), 8.63 (dd, J=8.4, 2.4Hz, 1H, ph-H), 8.46 (d, J=2.4Hz, 1H, ph-H), 8.35 (d, J=3Hz, 1H, ph-H), 8.28 (dd, J=8.1, 2.7Hz, 1H, ph-H), 7.40 (d, J=9Hz, 1H, ph-H), 4.29 (m, 2H, -CH2-), 2.68 (s, 3H, thiazole-CH3), and 1.29 (t, J=7.1Hz, 3H, -CH3). 13C NMR (150MHz, DMSO?d6): delta 188.06, 166.33, 161.59, 160.86, 152.17, 150.23, 148.54, 140.36, 134.32, 133.97, 132.68, 130.85, 129.99, 128.72, 128.17, 125.05, 121.68, 61.89, 17.60, and 14.54. High-resolution mass spectrometry (HRMS): m/z [M + Na]+ calcd. for [C20H15N3O10S2+Na]+: 544.0091, found: 544.0090. IR (KBr, cm?1): 3417.39, 3105.18, 2925.38, 1709.48, 1603.25, 1556.83, 1542.6, 1373.73, 1350.08, 1258.92, 1202.38, 1169.51, 1098.66, 887.35, 831.21, 710.78, 614.90, and 561.00., 161798-01-2

As the paragraph descriping shows that 161798-01-2 is playing an increasingly important role.

Reference£º
Article; Wang, Yi; Wang, Lijun; Jiang, Erkang; Zhu, Meiqing; Wang, Zhen; Fan, Shisuo; Gao, Qian; Liu, Shangzhong; Li, Qing X.; Hua, Rimao; Dyes and Pigments; vol. 156; (2018); p. 338 – 347;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.777-12-8,6-(Trifluoromethyl)benzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

Example 2: General procedure for synthesis of compounds 24 and 46. (0108) (0109) General methodology: In a microwave vial benzothiazole derivative and the corresponding isocyanate is added in each case. Next, THF is added as solvent. The vial is introduced into the microwave reactor and heated to the temperature for the time indicated in each case. After the reaction time, ethyl acetate (50 mL) and water (50 mL) is added. The organic phase is dried over anhydrous MgS04 and the solvent is removed under reduced pressure. The obtained residue was purified by flash column chromatography using Isolera One equipment, in all cases a mixture of hexane and ethyl acetate as eluent was used. N-(6-trifluoromethylbenzothiazole-2-yl)-N’-(3-chlorophenyl)urea (24): (0110) Reagents: 1-isocianato-3-chlorobenzene (175.8 mg, 1.2 mmol), 2-amino-6-trifluoromethylbenzothiazole (250 mg, 1.2 mmol) and THF (0.4 mL). Reaction conditions: 3 hours and 30 min under microwave irradiation at 110¡ãC. Purification by flash column chromatography using hexane/ethyl acetate (3:1) to obtain a white solid. Yield: 43.2 mg, 10percent. Mp: 222¡ãC-223¡ãC 1H NMR (500 MHz, DMSO-d6) delta: 11.16 (s, 1 H), 9.38 (s, 1 H), 8.41 (s, 1 H), 7.73 (s, 1 H), 7.69 (dd, J = 8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.35 (t, J = 7.9 Hz, 2H), 7.11 (d, J = 8.5 Hz, 1H). 13C NMR (126 MHz, DMSO-d6) delta: 162.6, 152.0, 140.3, 133.7, 131.0, 125.0 (q, J = 271.7 Hz), 123.6 (d, J = 31.8 Hz), 123.5, 123.4 (d, J = 2.5 Hz), 120.1 (d, J = 4.3 Hz), 118.8, 117.9. HPLC purity: >99percent. MS (ES) m/z: 372 [M+H]+., 777-12-8

777-12-8 6-(Trifluoromethyl)benzo[d]thiazol-2-amine 2735955, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; Consejo Superior De Investigaciones Cientificas (CSIC); MARTINEZ GIL, Ana; PEREZ FERNANDEZ, Daniel Ignacio; GIL AYUSO-GONTAN, Carmen; GARCIA SALADO, Irene; REDONDO SANCHO, Miriam; PEREZ MARTINEZ, Concepcion; EP2949651; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica