Analyzing the synthesis route of 14190-59-1

14190-59-1, 14190-59-1 Thiazole-2-carboxylic acid 2762733, athiazole compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14190-59-1,Thiazole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Compound 1 (3mmol), compound 2 (3mmol), N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (3.3mmol) and N,N-dimethyl pyridine (DMAP) (0.3mmol) were mixed with a molecular sieve, and the resulted mixture was cooled in ice bath (0°C). Then DMF and pyridine (4.5mmol) were added in turn. The progress of reaction was tracked by TLC. After the reaction was completed, the reactant was diluted with water and extracted with EtOAc. The solvent was removed completely by concentration. Then compound 3 was obtained through column chromatograph (yield 60percent). Subsequently, compound 3 (0.3mmol) was mixed with ammonium acetate (NH4OAc) (15mmol) and sodium acetate (NaOAc) (30mmol) and heated to 130°C, and the progress of reaction was tracked by TLC. Then the reactant was cooled to room temperature, and diluted with water, extracted with ethyl acetate. The solvent was removed completely by concentration. Then compound 4i (Wang279-1) was obtained by separation through column chromatograph with petroleum ether/ ethyl acetate (volume ratio 1:1) (yield 31percent).

14190-59-1, 14190-59-1 Thiazole-2-carboxylic acid 2762733, athiazole compound, is more and more widely used in various fields.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; EP1889843; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Downstream synthetic route of 14190-59-1

The synthetic route of 14190-59-1 has been constantly updated, and we look forward to future research findings.

14190-59-1, Thiazole-2-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

14190-59-1, Compound 1 (3 mmol), compound 2 (3 mmol), N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (3.3 mmol) and N,N-dimethylpyridine (DMAP) (0.3 mmol) were mixed with a molecular sieve, and the resulted mixture was cooled in ice bath (0° C.). Then DMF and pyridine (4.5 mmol) were added in turn. The progress of reaction was tracked by TLC. After the reaction was completed, the reactant was diluted with water and extracted with EtOAc. The solvent was removed completely by concentration. Then compound 3 was obtained through column chromatograph (yield 60percent). Subsequently, compound 3 (0.3 mmol) was mixed with ammonium acetate (NH4OAc) (15 mmol) and sodium acetate (NaOAc) (30 mmol) and heated to 130° C., and the progress of reaction was tracked by TLC. Then the reactant was cooled to room temperature, and diluted with water, extracted with ethyl acetate. The solvent was removed completely by concentration. Then compound 4i (Wang279-1) was obtained by separation through column chromatograph with petroleum ether/ethyl acetate (volume ratio 1:1) (yield 31percent).

The synthetic route of 14190-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; US2008/306121; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Simple exploration of 14190-59-1

As the paragraph descriping shows that 14190-59-1 is playing an increasingly important role.

14190-59-1, Thiazole-2-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Benzoic aldehyde (25 mmol) was added to the 25percent ammonia water solution (20 mL) containing potassium cyanide (KCN) (30 mmol) and ammonium chloride (37.5 mmol). The resulted mixture was stirred for 56 hours, and the reaction was tracked by TLC. The reactant was extracted with dichloromethane. Then the extract was dried over magnesium sulphate (MgSO4), and the solvent was concentrated to obtain compound 9 (2.9 g, yield 90percent). Compound 9 (6 mmol) was mixed with EDC (7.8 mmol), DMAP (0.6 mmol) and thiazole-2-formic acid (6 mmol). The resulted mixture was cooled under ice bath (0° C.), subsequently DMF was added thereto (15 mL). The progress of reaction was tracked by TLC. After the reaction was completed, the reactant was diluted with water, and extracted with ethyl acetate. The solvent was removed completely by concentration, and compound 10 was obtained by separation through column chromatograph (0.76 g, yield 50). Compound 10 (3.1 mmol) was mixed with triphenylphosphine (Ph3P) (7.75 mmol) and carbon tetrachloride (CCl4) (7.75 mmol), and the resulted mixture was dissolved in acetonitrile (20 mL). The reaction was conducted at 45° C. and tracked by TLC. After the reaction was completed, the solvent was removed by concentration, and compound 11 (Wang261) (yield 60percent) was obtained by separation through column chromatograph with petroleum ether/ethyl acetate (volume ratio 5:1). The following compounds were synthesized by the same method:, 14190-59-1

As the paragraph descriping shows that 14190-59-1 is playing an increasingly important role.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; US2008/306121; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

New learning discoveries about 14190-59-1

The synthetic route of 14190-59-1 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14190-59-1,Thiazole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Benzoic aldehyde (25mmol) was added to the 25percent ammonia water solution (20mL) containing potassium cyanide (KCN) (30mmol) and ammonium chloride (37.5mmol). The resulted mixture was stirred for 56 hours, and the reaction was tracked by TLC. The reactant was extracted with dichloromethane. Then the extract was dried over magnesium sulphate (MgSO4), and the solvent was concentrated to obtain compound 9 (2.9g, yield 90percent). Compound 9 (6mmol) was mixed with EDC (7.8mmol), DMAP (0.6mmol) and thiazole-2-formic acid (6mmol). The resulted mixture was cooled under ice bath (0°C), subsequently DMF was added thereto (15mL). The progress of reaction was tracked by TLC. After the reaction was completed, the reactant was diluted with water, and extracted with ethyl acetate. The solvent was removed completely by concentration, and compound 10 was obtained by separation through column chromatograph (0.76g, yield 50). Compound 10 (3.1mmol) was mixed with triphenylphosphine (Ph3P) (7.75mmol) and carbon tetrachloride (CCl4) (7.75mmol), and the resulted mixture was dissolved in acetonitrile (20mL). The reaction was conducted at 45°C and tracked by TLC. After the reaction was completed, the solvent was removed by concentration, and compound 11 (Wang261) (yield 60percent) was obtained by separation through column chromatograph with petroleum ether/ ethyl acetate (volume ratio 5:1)., 14190-59-1

The synthetic route of 14190-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; EP1889843; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Downstream synthetic route of 14190-59-1

14190-59-1, The synthetic route of 14190-59-1 has been constantly updated, and we look forward to future research findings.

14190-59-1, Thiazole-2-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 37 { (S)-3- [3- (4-Fluoro-phenyl)-l, 2, 4-oxadiazol-5-yl]-piperidin-1-yl}-thiazol-2-yl- methanone The compound was prepared following the procedure described in the Example 36, using 2-thiazolecarboxylic acid as the acid of choice and S-3- [3- (4-fluoro-phenyl)- [1, 2,4] oxadiazol-5-yl] -piperidine hydrochloride (prepared as described in the Example 12). Yield: 55 percent (off-white powder); mp=94-95°C ; [a] D20 = +127° (c=0. 9, CHCl3) ; LCMS (Tr): 5.54 min (Method A); MS (ES+) gave m/z : 359. 1. H-NMR (CDC13, 300 MHz), 8 (ppm): 8.05 (m br, 2H); 7. 89 (m br, 1H); 7.53 (m br, 1H); 7.15 (dd, 2H); 5.41, 4.94, 4.38, 4.04 and 3.44 (m br, 3H); 3.34 (m br, 2H); 2.36 (m, 1H); 2.13-1. 92 (m br, 2H); 1.78 (m, 1H).

14190-59-1, The synthetic route of 14190-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2005/44797; (2005); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 14190-59-1

14190-59-1, 14190-59-1 Thiazole-2-carboxylic acid 2762733, athiazole compound, is more and more widely used in various fields.

14190-59-1, Thiazole-2-carboxylic acid is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thiazole-2-carboxylic acid (3-acetyl-2, 4-difluoro-phenyl)-amide, which has the structural formula was made as follows. To thiazole-2-carboxylic acid (491 mg, 3.80 mmol ; Metzger, et AL., Bull. Soc. Chim. Fr. , 708-709 (1953) and FOR 1H NMR, see Borgen et AL., Acta. Chem. Scand. , 20; 2593-2600 (1966) ) in THF (2 mL) was added 0- (7- AZABENZOTRIAZOL-1-YL)-N, N, N’, N’-tetramethyluronium hexafluorophosphate (HATU; 1.45 g, 3.81 MMOL), followed by addition of 3′-amino-2′, 6 -DIFLUORO-ACETOPHENONE (from Example H (1) ; 542 mg, 3.36 MMOL) and triethylamine (0.88 mL, 6.3 MMOL). The mixture stirred under argon overnight, then partitioned between ethyl acetate and sat. aq. NA2CO3. The organic layer was separated, washed with 1 N HCI, dried over NA2SO4, and concentrated to afford a residue that was purified via column chromatography to afford 823 mg (92percent yield) of white solid, which was used without further purification. 1H NMR: 8 9. 33 (1H, bs), 8.54 (1H, td, J = 5.7, 9.0 Hz), 7.96 (1H, d, J = 3.1 Hz), 7.67 (1H, d, J = 3. 1 Hz), 7.02 (1H, td, J = 1. 8,9. 0 HZ), 2.64 (3H, t, J = 1. 8 HZ). THIAZOLE-2-CARBOXYLIC acid [3- (2-BROMOACETYL)-2, 4-DIFLUORO-PHENYL]-AMIDE, which has the structural formula was made as follows. To THIAZOLE-2-CARBOXYLIC acid [3- (2- ACETYL)-2, 4-difluoro-phenyl]-amide (530 mg, 1.88 MMOL) in HOAC (5 mL) was added pyridinium tribromide (600 mg, 1.88 MMOL). The mixture was heated at 70 C for a half hour, allowed to cool, and partitioned between ether and water. The organic layer was separated, washed with water and sat. aq. NaHCO3, dried over MGS04, and concentrated in vacuo to give 645 mg (95percent) of white solid, which was used without further purification. 1H NMR: No. 9.53 (1H, bs), 8.63 (1H, td, J = 5.8, 9.0 Hz), 7.96 (1H, d, J = 3.1 Hz), 7.69 (1H, d, J = 3. 1 Hz), 7.07 (1H, td, J = 1. 9,9. 0 HZ), 4.38 (2H, d, J = 0. 8 HZ). The title compound was made analogously to 4- [4-AMINO-5- (2, 6-DIFLUORO-BENZOYL)- thiazol-2-ylamino]-benzenesulfonyl fluoride from Example A (1). 4-ISOTHIOCYANATO- benzenesulfonamide (142 mg, 0.663 MMOL) and thiazole-2-carboxylic acid [3- (2-bromoacetyl)- 2, 4-difluoro-phenyl]-amide (300 mg, 0. 831 MMOL) gave 245 mg (69percent yield) of a yellow solid. 1H NMR (DMSO-d6) : 8 11.19 (1 H, s), 10.60 (1 H, s), 8.45 (2H, bs), 8.17 (1H, d, J = 3.1 Hz), 8.13 (1H, d, J = 3. 1 Hz), 7.80 (1H, d, J = 9. 2 HZ), 7.76 (1H, d, J = 9. 2 HZ). HRESIMS : calcd. for C20H5F2N603S3 : 537.0285. Found: 537.0272. ANAL. CALCD. for C20HA4F2N604S3 0. 4 H2ONo.0. 1 EtOH : C, 44.24 ; H, 2.83 ; N, 15. 33; S, 17.54. Found: C, 44.23 ; H, 2.64 ; N, 15.16 ; S, 17.33.

14190-59-1, 14190-59-1 Thiazole-2-carboxylic acid 2762733, athiazole compound, is more and more widely used in various fields.

Reference:
Patent; PFIZER INC.; WO2004/72070; (2004); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Some tips on 14190-59-1

14190-59-1, As the paragraph descriping shows that 14190-59-1 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14190-59-1,Thiazole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Preparation 107: 1, 3-thiazole-2-carbonyl CHLORIDE 1,3 thiazole-2-carboxylic acid (Preparation 92,5. 0 g, 39 MMOL) was added to a solution containing sodium hydroxide (1.55 g), in water (26 ml). The solution was evaporated to dryness and the resultant solid was triturated with diethyl ether, filtered and dried in an oven at 60 C for 6 h to give a brown solid (5.5 g). The solid was added to thionyl chloride (25 ML) and heated on a steam bath for 2 h. The excess thionyl chloride was removed in vacuo and the resultant oil was triturated with petroleum ether (40-60,3 x 30 ml) to give the title compound as an oily solid upon filtration and evaporation (4.0 g, 70percent).

14190-59-1, As the paragraph descriping shows that 14190-59-1 is playing an increasingly important role.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/72086; (2004); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica