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CAS No. : | 873436-89-6 | MDL No. : | MFCD25968211 |
Formula : | C12H8IN5O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 413.19 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
62.8% | With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 2h; | Step 14b. 2-(6-Amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)ethyl acetate (Compound 401-38); A mixture of compound 105-38 (3.89 g, 9.41 mmol), Cs2CO3 (3.68 g, 11.3 mmol), 2-<strong>[927-68-4]bromoethyl acetate</strong> (1.89 g, 11.3 mmol) and anhydrous DMF (50 mL) was stirred for 2 h at 50 C. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel (CH2Cl2/MeOH=60/1) to provide target compound 401-38 as a pale yellow solid (2.95 g, 62.8%): LCMS: 500 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; | A solution of 8-(6-iodo-benzo[1 ,3]dioxol-5-ylsulfanyl)-9H-puhn-6-ylamine previously prepared (cf. Chiosis G. et al., "Identification of Potent Water Soluble Purine-Scaffold Inhibitors of the Heat Shock Protein 90", J. Med.Chem. 2006, vol. 49, no. 1 , p. 381 (0.3 g, 0.73 mmol), toluene-4-sulfonic acid butyl ester previously prepared (cf. Sekera, V. et al., "Higher alkyl sulfonates", J. Am. Chem. Soalpha, 1993, vol. 55, p. 345 (0.7 g, 1.8 mmol), and Cs2CO3 (0.4 g, 1.7 mmol) in 7 ml_ of DMF was stirred at 8O0C for 16 h. Removal of the solvent and purification by chromatography on silica (CHCI3ZAcOEt/ MeOH, 5:4:1 ) yielded 9-Butyl-8-(6-iodo-benzo[1 ,3]dioxol-5-ylsulfanyl)-9H-purin-6- ylamine (0.17 g, 49%) as a viscous oil . 1H-NMR [ CDCI3, delta, ppm]: 8.32 (s, <n="36"/>1 H), 7.29 (s, 1 H), 7.19 (s, 1 H), 5.97 (s, 2H, OCH2O), 4.20 (m, 2H, CH2N), 1.76 (m, 2H, CH2), 1.40 (m, 2H, CH2), .1.37 (m, 3H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With caesium carbonate In N,N-dimethyl-formamide at 20℃; | 3-(6-Amino-8-((6-iodobenzo[ifl[l,3]dioxol-S-yl)thio)-9jBr-purin-9-yI)-iV-(tert- butyl)propane-l-sulfonamide (WSS3). To a solution of 8-((6-iodobenzo[if)[l,3]dioxol-5- yl)thio-9i/-purin-6-amine (56 mg, 0.13 mmol) in DMF ( 2 mL) was added Af-t-butyl-3- chloro- -propane-l -sulfonamide (144 mg, 0.65 mmol) and Cs2C03 (88 mg, 0.27 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was condensed under vacuum and the residue was purified by Prep TLC (CH2Cl2:NH3-MeOH (7N), 20:1) to yield WS53 as a white solid (18 mg, 22%). NMR (600 MHz,CDCl3/MeOH-^): δ 8.21 (s, 1H), 7.40 (s, 1H), 7.06 (s, 1H), 6.06 (s, 2H), 4.38 (t, /= 7.3 Hz, 2H), 3.12 (t, J = 7.4 Hz, 2H), 2.13-2.44 (m, 2H), 1.33 (s, 9H); 13C NMR (150 MHz, CDCla/MeOH-rfi): δ 155.8, 153.8, 152.4, 151.5, 151.0, 149.0, 126.7, 121.0, 120.8, 115.3, 104.1, 95.7, 55.7, 51.1, 43.6, 31.5, 25.9; HRMS (ESI) m/z [M+H]+ calcd. forC19H24l 604S2, 591.0345; found 591.0361. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 6-(6-Amino-8-(6-iodobenzo[d][l,3]dioiol-5-ylthio)-9H-purin-9-yl)hexanamide [DZ5- 49-N9]. 50 mg (0.121 mmol) of 8-(6-iodobenzo[d][l,3]dioxol-5-ylthio)-9H-purin-6-amh e (S13-1) was dissolved in DMF (2 mL). 47 mg (0.145 mmol) of Cs2C03 and 117.4 mg (0.605 mmol) of 6-bromohexanamide (S13-2) were added and the mixture was stirred at rt for 2 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (CH2Cl2:MeOH-NH3 (7N), 10:1) to give 12.7 mg (20%) ofDZS-49- N9. 'H NM (500 MHz, CDCl3/MeOH-i¾): δ 8.13 (s, 1H), 7.31 (s, 1H), 6.97 (s, 1H), 5.98 (s, 2H), 4.13 (t, J= 7.6 Hz, 2H), 2.14 (t, J= 7.6 Hz, 2H), 1.71-1.80 (m, 2H), 1.55-1.65 (m, 2H), 1.28-1.39 (m, 2H); HRMS (ESI) m/z [M+H]+ calcd. for CigHjoINeCbS, 527.0362; found 527.0364. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With cesium carbonate; In N,N-dimethyl-formamide; for 1.5h;Sonication; | 200 mg (0.484 mmol) of Compound 11 was dissolved in DMF (8 mL).466 mg (1.43 mmol) of Cs2C03 and 819 mg (2.42 mmol) <strong>[17702-83-9]N-(8-bromooctyl)phthalimide</strong> were addedand the mixture was sonicated for 1.5 h. Solvent was removed under reduced pressure and theresulting residue was purified by preparatory TLC (CH2Cl2:MeOH:AcOH, 15:1 :0.5) to give 120 mg(34percent) of Compound Hie. 1HNMR (500 MHz, CDC,) o 8.29 (s, H), 7.84 (dd, J= 5.5, 3.1 Hz, 2H),7.70 (dd,J= 5.5, 3.1 Hz, 2H), 7.28 (s, H), 6.87 (s, H), 6.29 (br s, 2H), 5.96 (s, 2H), 4.18 {t, J= 7.5Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 1.62-1.77 {m, 4H), 1.25-1.36 (m, 8H); MS {ESI) mlz 671.3 [M+Ht, |
34% | With caesium carbonate; In N,N-dimethyl-formamide; for 1.5h;Sonication; | 200 mg (0.484 mmol) of 112 was dissolved in DMF (8 mL). 466 mg (1.43 mmol) of CS2CO3 and 819 mg (2.42 mmol) <strong>[17702-83-9]N-(8-bromooctyl)phthalimide</strong> were added and the mixture was sonicated for 1.5 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (CH2Cl2:MeOH:AcOH, 15: 1 :0.5) to give 120 mg (34percent) of 113d. lH NMR (500 MHz, CDC13) delta 8.29 (s, 1H), 7.84 (dd, J= 5.5, 3.1 Hz, 2H), 7.70 (dd, J= 5.5, 3.1 Hz, 2H), 7.28 (s, 1H), 6.87 (s, 1H), 6.29 (br s, 2H), 5.96 (s, 2H), 4.18 (t, J= 7.5 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 1.62- 1.77 (m, 4H), 1.25- 1.36 (m, 8H); MS (ESI) m/z 671.3 [M+H]+. |
34% | With caesium carbonate; In N,N-dimethyl-formamide; for 1.5h;Sonication; | 2-(8-(6-Amino-8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-9H-purin-9-yl)octyl)isoindoline-1,3-dione (16c) (Scheme 4). 200 mg (0.484 mmol) of Compound 11 was dissolved in DMF (8 mL). 466 mg (1.43 mmol) of Cs2CO3 and 819 mg (2.42 mmol) <strong>[17702-83-9]N-(8-bromooctyl)phthalimide</strong> were added and the mixture was sonicated for 1.5 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (CH2Cl2:MeOH:AcOH, 15:1:0.5) to give 120 mg (34percent) of Compound 16c. 1H NMR (500 MHz, CDCl3) delta 8.29 (s, 1H), 7.84 (dd, J = 5.5, 3.1 Hz, 2H), 7.70 (dd, J = 5.5, 3.1 Hz, 2H), 7.28 (s, 1H), 6.87 (s, 1H), 6.29 (br s, 2H), 5.96 (s, 2H), 4.18 (t, J = 7.5 Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 1.62-1.77 (m, 4H), 1.25-1.36 (m, 8H); MS (ESI) m/z 671.3 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; |