Home Cart Sign in  
Chemical Structure| 650579-82-1 Chemical Structure| 650579-82-1

Structure of 650579-82-1

Chemical Structure| 650579-82-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 650579-82-1 ]

CAS No. :650579-82-1
Formula : C14H21ClN2O2S
M.W : 316.85
SMILES Code : O=C(N1CCC(C2=NC(CCl)=CS2)CC1)OC(C)(C)C
MDL No. :MFCD20040373

Safety of [ 650579-82-1 ]

Application In Synthesis of [ 650579-82-1 ]

* 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.

  • Downstream synthetic route of [ 650579-82-1 ]

[ 650579-82-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 214834-18-1 ]
  • [ 534-07-6 ]
  • [ 650579-82-1 ]
YieldReaction ConditionsOperation in experiment
92% With magnesium sulfate; magnesium carbonate; In acetone; for 12h;Reflux; Inert atmosphere; To a solution of compound9(1.3 g, 5.3 mmol) in acetone (50 mL) was added MgSO4(1.6 g, 13.2 mmol), MgCO3(534 mg, 6.3 mmol) and 1,3-dichloroacetone (1.1 g, 9.0 mmol). The resulting reaction mixture was heated under reflux overnight, cooled to room temperature and filtered through a celite. The solvent was removed by evaporation and the residue was dissolved with EtOAc. The resulting solution was washed with 5% NaHSO3(2 x 50 mL), saturated NaHCO3and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered, and concentrated to afford compound10(1.5 g, 92%).1H-NMR (CDCl3,300 MHz) δ 7.19 (1H, s, thiazole), 4.66 (2H, s, CH2), 4.22 (2H, d,J= 12.0 Hz, CH2), 3.19 (1H, tt,J= 9.0 Hz, 3.0 Hz, CH), 2.91 (2H, t,J= 12.0 Hz, CH2), 1.70 (2H, dt,J= 12.0 Hz, 3.0 Hz, CH2), 1.47 (9H, s, C(CH3)3).
92.7% With magnesium sulfate; magnesium carbonate; In acetone; at 65℃; for 4h; Compound 2 (10 g, 0.04 mol) was added to a solution of 1,3-dichloroacetone(6.6 g, 0.052 mol), MgSO4 (7.2 g, 0.06 mol) and MgCO3 in acetone (60 mL). The resulting solution was heated to 65 C and stirred at this temperature for 4 h, and monitored by TLC, then concentrated. The residue was diluted with EA (80 mL), washed with brine, dried over Na2SO4, filtered and concentrated to afford compound 3 (12 g, 92.7% yield)as a yellow oily liquid. 1H NMR (400 MHz, CDCl3) δ 7.20(s, 1H), 4.67(s, 2H), 3.16(tt, J = 11.7 Hz, 3.8 Hz, 1H), 2.87(d, J = 3.2 Hz, 3H), 2.11-2.07(m, 2H), 1.71(qd, J = 12.5 Hz, 4.5 Hz, 3H), 1.47(s, 9H).
77.38% In toluene; for 10h;Reflux; 4-aminothiocarbonyl tetrahydropyridine-1(2H)-tert-butyl formate (3.00g, 12.28mmol)And 1,3-dichloroacetone (1.71g, 13.51mmol) dissolved in toluene,Heat up to reflux reaction, after 10h, TLC detects that the reaction is complete,Concentrate under reduced pressure to remove toluene, then add 100 mL of ethyl acetate for extraction,The organic layer was washed with water and saturated brine, and dried overnight with anhydrous Na2SO4.Filter out the desiccant, concentrate under reduced pressure to evaporate the solvent,The residue was purified by silica gel column chromatography,3.01g of the final product was obtained, and the yield was 77.38%.
With magnesium sulfate; magnesium carbonate; In acetone;Heating / reflux; Preparation of Intermediate 1: 4-(4-Chloromethyl-thiazol-2-yl)-piperidine-l-carboxylic acid tert-butyl ester; To a solution of 4-thiocarbamoyl-piperidine-l-carboxylic acid tert-butyl ester (4.9 g, 20 mmol) in acetone (80 raL) was added 1 ,3-dichloroacetone (3.3 g, 26 mmol), MgSO4 (3.6 g, 30 mmol) and MgCO3 (1.68 g, 20 mmol). The mixture was heated under reflux overnight, cooled and filtered through celite. The solvent was removed in vacuo and the residue was redissolved with EtOAc (150 mL). The resulting solution was washed successively with 5% NaHSO3, saturated NaHCO3, and brine. After drying (Na2SO4), the solvent was removed to afford the desired product. 1H NMR (CDCl3): δ 7.20 (IH, s), 4.67 (2H, s), 4.20 (2H, br), 3.16 (IH, m), 2.87 (2H, m), 2.09 (2H, m), 1.72 (2H, m), 1.47 (9H, s).
With magnesium sulfate; magnesium carbonate; In acetone;Reflux; Example 3b [0033] To a 500 mL flask under air, immersed in an oil bath and a condenser, was added 4-thiocarbamoyl-piperidine-l-carboxylic acid tert-butyl ester (29 g, 120mmol), acetone (300 mL) MgS04 (21.6g, 180 mmol) and MgC03 (10 g, 120 mmol), 1,3- dichloroacetone (19.8 g, 156 mmol). The resulting mixture was heated under reflux overnight, cooled and filtered through celite. The solvent was removed in vacuo and the residue was redissolved with EtOAc (500 mL). The resulting solution was washed successively with 5% NaHS03 (twice), saturated NaHC03 and brine. After drying (NaS04), the solvent was removed to afford 35 g of the title compound as light yellow oil. The oil became dark solid after standing at room temperature. The color could be removed by activated charcoal. The purity was improved from 92% to 96%.1H NMR (CDC13): δ 7.20 (1H, s), 4.67 (2H, s), 4.20 (2H, br), 3.16 (1H, m), 2.87 (2H, m), 2.09 (2H, m), 1.72 (2H, m), 1.47 (9H, s).
With magnesium sulfate; magnesium carbonate; In acetone;Reflux; To a 500 mL flask under air, immersed in an oil bath and a condenser, was added 4-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (29 g, 120 mmol), acetone (300 mL) MgSO4 (21.6 g, 180 mmol) and MgCO3 (10 g, 120 mmol), 1,3-dichloroacetone (19.8 g, 156 mmol). The resulting mixture was heated under reflux overnight, cooled and filtered through celite. The solvent was removed in vacuo and the residue was redissolved with EtOAc (500 mL). The resulting solution was washed successively with 5% NaHSO3 (twice), saturated NaHCO3 and brine. After drying (NaSO4), the solvent was removed to afford 35 g of the title compound as light yellow oil. The oil became dark solid after standing at room temperature. The color could be removed by activated charcoal. The purity was improved from 92% to 96%. 1H NMR (CDCl3): δ 7.20 (1H, s), 4.67 (2H, s), 4.20 (2H, br), 3.16 (1H, m), 2.87 (2H, m), 2.09 (2H, m), 1.72 (2H, m), 1.47 (9H, s).
Example 36 N-(3,4-dichlorophenyl)-6-(methyloxy)-7-([2-(1-methylpiperidin-4-yl)-1,3-thiazol-4-yl]methyl}oxy)quinazolin-4-amine hydrochloride 1,1-Dimethylethyl 4-(aminocarbonothioyl)piperidine-1-carboxylate (1.50 g, 6.14 mmol), NaHCO3 (0.570 g, 6.78 mmol) and 1,3-dichloroacetone (0.860 g, 6.77 mmol) were combined in 1,2-dichloroethane (4 mL) and the reaction mixture was stirred at room temperature for 12 h. The crude reaction mixture was filtered using CH2Cl2 and the filtrate was concentrated in vacuo until approximately 30 mL of solvent remained. To this solution was added pyridine (0.75 mL, 9.2 mmol), and the solution was cooled with an ice bath. Thionyl chloride (0.49 mL, 6.8 mmol) was added and the solution was allowed to warm slowly to room temperature. The solvent was removed in vacuo and the residue was taken up in 10% MeOH/ethyl acetate (100 mL). The organic layer was washed with H2O (100 mL) and brine (100 mL), dried (Na2SO4), filtered, and concentrated in vacuo to yield 2.24 g (>100%) of crude 1,1-dimethylethyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate as a colorless oil. 1H NMR (400 MHz, d6-DMSO): 7.62 (s, 1H), 4.60 (s, 2H), 3.98 (m, 1H), 3.63 (dd, 2H), 3.16 (m, 1H), 2.90 (broad s, 2H), 2.01 (dd, 1H), 1.51 (m, 2H), 1.40 (s, 9H). MS (EI) for C14H21N2O2SCl: 261 (M-tBu).
With magnesium sulfate; magnesium carbonate; In acetone;Reflux; To a solution of 4-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (4.9 g, 20 mmol) in acetone (80 mL) was added 1,3-dichloroacetone (3.3 g, 26 mmol), MgSO4 (3.6 g, 30 mmol) and MgCO3 (1.68 g, 20 mmol). The mixture was heated under reflux overnight, cooled and filtered through celite. The solvent was removed in vacuo and the residue was redissolved with EtOAc (150 mL). The resulting solution was washed successively with 5% NaHSO3, saturated NaHCO3, and brine. After drying (Na2SO4), the solvent was removed to afford the desired product. ‘HNMR(CDC13): ö 7.20 (1H, s), 4.67 (2H, s), 4.20 (2H, br), 3.16 (1H, m), 2.87 (2H, m), 2.09 (2H, m), 1.72 (2H, m), 1.47 (9H, s)

 

Historical Records