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CAS No. : | 223575-69-7 | MDL No. : | MFCD06657778 |
Formula : | C10H7NOS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PFOXNJMCQNJJES-UHFFFAOYSA-N |
M.W : | 189.23 | Pubchem ID : | 15532482 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A To a mixture of 2-bromothiazole (826 mg, 4.99 mmol) and tetrakis(triphenylphosphine) palladium (0) (175 mg, 0.151 mmol) in 1,2-dimethoxyethane (20 mL) was added 2-formylbenzeneboronic acid (0.9017 g, 6.01 mmol) and 1 N aqueous NaHCO3 (8 mL). The resultant mixture was heated at reflux for 6 hrs. The reaction mixture was diluted with water and extracted with EtOAc (2*50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane) to yield 2-(2-thiazolyl)benzaldehyde as a white solid. MS (loop pos) MH+=190.1 1H NMR (300 MHz, CDCl3) 7.50 (m, 1H), 7.55-7.60 (m, 1H), 7.65-7.70 (m, 1H), 7.75-7.80 (m, 1H), 7.95-7.97 (m, 1H), 8.00-8.05 (m, 1H), 10.5 (s, 1H) | ||
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; for 5h;Inert atmosphere; Reflux; | General procedure: Ethanol (500 mE), boronic acid Ar2-B(OH)2 (92.7 mmol, 1.2 eq) and bromoarylaldehyde or bromoheteroarylaldehyde Br-Ar,--CHO (77.3 mmol) are introduced in succession into a 1 E flask under argon and at ambient temperature. The solution is degassed with argon for 15 minutes. Pd(PPh3)4 (1.78 g, 1.55 mmol) and Na2CO3 (92.7 mE of a 2M solution in H20, 185 mmol, 2.4 eq) are then introduced in a single portion. Afier the addition, the reaction mixture is heated at reflux for 5 hours. The mixture is then evaporated to dryness. The residue is taken up in DCM (1 E) and H20 (200 mE). After decantation, the aqueous phase is extracted with DCM (200 mE). The organic phases are combined and then washed with a saturated NaC1 solution (400 mE), dried over Mg504 and concentrated under reduced pressure. The residue is then purified by flash chromatography on silica gel. The expected product is obtained with yields of from 59 to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium tris(acetoxy)borohydride; In CHCl3:CH3OH; diethyl ether; 1,2-dichloro-ethane; | Step B To a mixture of <strong>[223575-69-7]2-(2-thiazolyl)benzaldehyde</strong> (200 mg, 1.06 mmol) and 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (0.232 mg, 1.00 mmol) in 1,2-dichloroethane (20 mL) was added sodium triacetoxyborohydride (376 mg, 1.79 mmol). The resultant mixture was stirred at room temperature for 18 h, quenched with aqueous NaHCO3 (50 mL) and extracted with CHCl3 (2*50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was dissolved in 1:1 CHCl3:CH3OH (30 mL) and treated with 2 mL of 1 N HCl in Et2O. The HCl salt was precipitated by addition of Et2O, collected by filtration and dried in the vacuum oven at 60 C. for 18 h to yield the product as an amorphous solid. MS (loop pos): MH+=405.1 (100%) 1H NMR (300 MHz, DMSO d6) 61.50-1.60 (m, 2H), 2.75-2.90 (m, 2H), 3.45-3.55 (m, 2H), 3.75-3.90 (m, 2H), 4.65 (s, 2H), 4.70 (s, 2H), 6.76-6.81 (m, 1H), 6.95-6.98 (m, 2H), 7.18-7.24 (m, 2H), 7.60-7.70 (m, 2H), 7.90-7.99 (m, 3H), 8.14-8.15 (m, 1H), 9.00 (s, 1H), 9.80 (br s, 1H exchangeable). | |
With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 18h; | Step B: To a mixture of <strong>[223575-69-7]2-(2-thiazolyl)benzaldehyde</strong> (200 mg, 1.06 mmol) and 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (.232 mg, 1.00 mmol) in 1,2-dichloroethane (20 mL) was added sodium triacetoxyborohydride (376 mg, 1.79 mmol). The resultant mixture was stirred at room temperature for 18h, quenched with aqueous NaHCO3 (50 mL) and extracted with CHCl3 (2 x 50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was dissolved in 1:1 CHCl3: CH3OH (30 mL) and treated with 2 mL of 1 N HCl in Et2O. The HCl salt was precipitated by addition of Et2O, collected by filtration and dried in the vacuum oven at 60C for 18h to yield the product as an amorphous solid. MS (loop pos): MH+ = 405.1 (100%) 1H NMR (300 MHz, DMSO d6) delta 1.50-1.60 (m, 2H), 2.75-2.90 (m, 2H), 3.45-3.55 (m, 2H), 3.75-3.90 (m, 2H), 4.65 (s, 2H), 4.70 (s, 2H), 6.76-6.81 (m, 1 H), 6.95-6.98 (m, 2H), 7.18-7.24 (m, 2H), 7.60-7.70 (m, 2H), 7.90-7.99 (m, 3H), 8.14-8.15 (m, 1H), 9.00 (s, 1H), 9.80 (br s, 1 H exchangeable). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 160℃; for 0.0833333h;Microwave irradiation; | 6.21. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles). Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture. The reactor was sealed, and the reaction was run under microwave at 160 C. for 5 minutes. LCMS shows completion of the reaction with desired product. The reaction mixture was then poured into a separation funnel. Then 200 ml of methylene chloride and 100 ml of water were added for extraction. The methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%). |
38% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In acetonitrile; at 160℃; for 0.0833333h;Sealed tube; Microwave irradiation; | To a 40 ml microwave reactor was added 1.04 g of 2-formylphenylboronic acid (6.9 mmol) of 1.14 g of 2-bromothiazole(6.9 mmol), 240 mg of bistriphenyl-phosphine palladium dichloride (Pd (PPh3) 2Cl2, 0.34 mmol). then,To the mixture was added 13.8 ml of 1 M Na2CO3 (13.8 mmol) and 10 ml of CH3CN. Sealed reactor,The reaction was run under microwave at 160 C for 5 minutes.LCMS shows the desired reaction of the desired product. The reaction mixture was then poured into a separation funnel. Add 200 ml of dichloromethaneAlkane and 100 ml of water for extraction. The dichloromethane layer was dried over MgSO4. The solvent was removed to give the crude product, which was passed through siliconThe column chromatography was eluted with a hexane / ethyl acetate mixture (5/1 to 2/1)To give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%). |
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; for 6h;Reflux; | Example 4 1-phenyl-8-[[2-(2-thiazolyl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one (Compound 24) Step A: To a mixture of 2-bromothiazole (826 mg, 4.99 mmol) and tetrakis(triphenylphosphine) palladium (0) (175 mg, 0.151 mmol) in 1,2-dimethoxyethane (20 mL) was added 2-formylbenzeneboronic acid (0.9017 g, 6.01 mmol) and 1 N aqueous NaHCO3 (8 mL). The resultant mixture was heated at reflux for 6 hrs. The reaction mixture was diluted with water and extracted with EtOAc (2 X 50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane) to yield 2-(2-thiazolyl)benzaldehyde as a white solid. MS (loop pos) MH+ = 190.1 1 H NMR (300 MHz, CDCl3) 7.50 (m, 1 H), 7.55-7.60 (m, 1 H), 7.65-7.70 (m, 1 H), 7.75-7.80 (m, 1 H), 7.95-7.97 (m, 1 H), 8.00-8.05 (m, 1 H), 10.5 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a 50 ml round bottom flask, 184 mg of <strong>[223575-69-7]2-thiazol-2-yl-benzaldehyde</strong> (0.97 mmole) and 10 ml of anhydrous tetrahydrofuran (THF) were added. Then, 145.4 mg of trifluoromethyltrimethylsilane (1.02 mmoles) and 20 mul of 1M tert-butylammonium fluoride in THF (0.02 mmole) were added to solution. The mixture was stirred at room temperature overnight, after which 10 ml of 1 N HCl was added and the reaction mixture was stirred at r.t. for 15 minutes. THF was removed in vacuo, and the mixture was extracted with methylene chloride (3*50 ml). The combined CH2Cl2 layer was dried over MgSO4. Removal of solvent gave 262 mg of crude product, which was about 95% pure, and was used in next step without further purification. 2,2,2-Trifluoro-1-(2-thiazol-2-yl-phenyl)-ethanol (260 mg, 1 mmole), (S)-3-[4-(2-amino-6-chloro-pyrimidin-4-yl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid (390 mg, 1 mmole), cesium carbonate (1.3 g, 4 mmoles) and 10 ml of 1,4-dioxane were mixed together in a 50 ml sealed tube. The reaction mixture was heated at 100 C. for 3 days. Water (20 ml) was added, and then 1N HCl aq. was added slowly to adjust the pH to 4, then the 1,4-dioxane was removed in vacuo and the resulting mixture was extracted with methylene chloride (3*50 ml). The combine methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was taken to next step reaction without further purification. The above crude product was dissolved in 5 ml of methylene chloride, and 0.4 ml of trifluoroacetic acid was added. The mixture was stirred at room temperature overnight. The trifluoroacetic acid was then removed in vacuo to give a crude product, which was purified by prep HPLC to give 63 mg of pure product. HPLC; YMC Pack ODS-A 3*50 mm, 7 um; Solvent A=water with 0.1% TFA; Solvent B=methanol with 0.1% TFA. Solvent B from 10 to 90% over 4 minutes; Flow rate=2 ml/min; RT=3 min. HPLC purity=100%. LCMS: M+1=515.9. 1H NMR (400 MHz, CD3OD) delta 8.06 ppm (2H, m); 7.92 (2H, d, J=8 Hz); 7.84 (1H, m); 7.81 (1H, m); 7.77 (1H, d, J=4 Hz); 7.57 (2H, m); 7.45 (2H, d, J=8 Hz); 6.84 (1H, s); 4.30 (2H, dd, J=8 Hz); 3.38 (2H, dd, J=12, 2 Hz); 3.23 (2H, dd, J=12, 8 Hz). | ||
To a 50 ml round bottom flask was added 184 mg of <strong>[223575-69-7]2-thiazol-2-yl-benzaldehyde</strong> (0.97 mmol) and 10 ml of anhydrous tetrahydrofuran(THF). then,To this solution was added 145.4 mg of trifluoromethyltrimethylsilane (1.02 mmol)And 20 mul of a 1 M solution of tert-butylammonium fluoride in THF (0.02 mmol). The mixture was stirred overnight at room temperature,Followed by the addition of 10 ml of 1N HCl, and the reaction mixture was stirred at room temperature for 15 minutes. The THF was removed in vacuo,The mixture was extracted with dichloromethane (3 x 50 ml).The combined CH2Cl2 layer was dried over MgSO4. The solvent was removed to give 262 mg of crude product with a purity of about 95%And used for the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In dichloromethane; water; acetonitrile; | 6.54. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxyl-pyrimidin-4-yl}-phenyl)-propionic acid To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles). Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture. The reactor was sealed, and the reaction was run under microwave at 160 C. for 5 minutes. LCMS shows completion of the reaction with desired product. The reaction mixture was then poured into a separation funnel. Then 200 ml of methylene chloride and 100 ml of water were added for extraction. The methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With perchloric acid; In ethanol; at 20℃; for 20h;Inert atmosphere; | The preparation of (2,6-dimethylphenyl)-(6-fluoro-2-(2-thiazol-2-ylphenyl)-imidazo[1,2-a]pyridin-3-yl]amine (A1) is carried out analogously to the following scheme:118 mg (1.0 mmol) of 2-amino-5-fluoropyridine and 189 mg (1.0 mmol) of <strong>[223575-69-7]2-thiazol-2-ylbenzaldehyde</strong> are dissolved successively in 5 ml of ethanol at RT under inert gas. 137 mg (1.0 mmol) of 2,6-dimethyiphenyl isocyanide are then added, 0.043 ml of 70% perchloric acid is added dropwise, and the mixture is stirred at RT for a further 20 h. 10 ml of petroleum ether are subsequently added, and the precipitated solid is filtered off with suction. This is triturated with a little ethyl acetate and filtered off with suction again, giving 177 mg (43%) of (2,6-dimethylphenyl)-[6-fluoro-2-(2-thiazol-2-yl-phenyl)imidazo[1,2-a]pyridin-3-yl]amine (A1) as solid; MS-FAB (M+H+)=415.7; Rf (polar method): 1.98 min;1H-NMR (DMSO-d6) d [ppm] 8.43 (1H, s), 8.03-8.07 (1H, m), 7.96 (1H, d, J=8.1 Hz), 7.92 (1H, d, J=3.3 Hz), 7.81 (1H, d, J=8.1 Hz), 7.77 (1H, d, J=3.3 Hz), 7.69 (1H, dd, J=9.7 and 5.1 Hz), 7.42 (1H, t, J=8.0 Hz), 7.29 (1H, ddd, J=2.4, 8.0 and 9.9 Hz), 7.28 (1H, s), 6.86 (2H, d, J=7.5 Hz), 6.65 (1H, t, J=7.5 Hz), 1.90 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With acetic acid; at 50 - 80℃; for 72h; | Example 26: 5-[l-tert-Butyl-2-(2-thiazol-2-yl-phenyl)-lH-benzimidazol-5-yl]- pyrimidin-2-ylamine A solution of <strong>[223575-69-7]2-thiazol-2-yl-benzaldehyde</strong> (100 mg, 0.53 mmol) and 4-(2-amino- pyrimidin-5-yl)-Nl-ieri-butyl-benzene-l,2-diamine (120 mg, 0.45 mmol) in acetic acid (5 mL) is warmed to 50 C for 12 hours and then at 80 C for 60 hours. After this time the reaction is cooled to room temperature and pour into water and NaHC03 (sat.). The product is extracted into EtOAc (3x) and the combined organics are dried (MgS04), filtered and concentrated. Purification via flash chromatography (12g silica gel, 0-5% MeOH/CH2Cl2) affords the title compound (30 mg, 16%). LCMS (ESMS): m/z 427.20 (M++l) |
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