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CAS No. : | 1012059-50-5 | MDL No. : | MFCD22571752 |
Formula : | C14H14N4OS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 286.35 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
77% | Stage #1: 4-chloro-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2(3H)-thione With ammonia; sodium amide at 20℃; for 30h; Stage #2: With ethanol at -40℃; | 23.d Step 23d. 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2(3H)-thione (Compound 605); A mixture of compound 604 (1 g, 3.25 mmol) and sodium amide (3 g, 77 mmol) in 25 mL liquid ammonia was charged in a no air sealed tube, and stirred at room temperature for 30 h. The mixture was cooled to -40° C. and the tube was opened. Ethanol was added carefully to the reaction until no gas generated. 200 mL of water was added and adjusted the mixture to pH 7 with acetic acid. The resulting mixture was filtered to obtain crude which was purified by column chromatography on silica gel (methylene chloride/methanol at 50:1) to obtain compound 605 as a white solid (718 mg, 77%): LCMS: 287 [M]+; 1H NMR (DMSO-d6): δ 3.68 (s, 3H), 5.31 (s, 2H), 6.06 (s, 2H), 6.59 (d, 1H, J=6.3 Hz), 6.85 (d, 2H, J=9.0 Hz), 7.33 (d, 2H, J=8.4 Hz), 7.64 (d, 1H, J=5.7 Hz), 12.53 (s, 1H). |
77% | Stage #1: 4-chloro-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2(3H)-thione With ammonia; sodium amide at 20℃; for 30h; Stage #2: With ethanol at -40℃; Stage #3: With water; acetic acid | 3.d' Step 3d'. 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2(3H)-thione (Compound 0204); A mixture of 0203 (1 g, 3.25 mmol) and sodium amide (3 g, 77 mmol) in 25 mL liquid ammonia was charged in an air free sealed tube. The mixture was then stirred at room temperature for 30 h. The mixture was cooled to -40° C. and then tube was opened. Ethanol was added carefully to terminate the reaction until no gas generated. Water (200 mL) was added and the mixture was adjusted to pH 7 with acetic acid. The resulting solid was filtered to obtain crude product which was purified by column chromatography on silica gel (methylene chloride/methanol at 50:1) to obtain the title compound 0204 as a white solid (718 mg, 77%): LCMS: 287 [M]+; 1H NMR (DMSO-d6) δ 3.68 (s, 3H), 5.31 (s, 2H), 6.06 (s, 2H), 6.59 (d, 1H, J=6.3 Hz), 6.85 (d, 2H, J=9.0 Hz), 7.33 (d, 2H, J=8.4 Hz), 7.64 (d, 1H, J=5.7 Hz), 12.53 (s, 1H). |
77% | With ammonia; sodium amide at 20℃; for 30h; Sealed tube; | 1.1e Step 1e. 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2(3H)-thione (Compound 0107) Step 1e. 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2(3H)-thione (Compound 0107) (0153) A mixture of 0106 (1 g, 3.25 mmol) and sodium amide (3 g, 77 mmol) in 25 mL liquid ammonia was charged in an air free sealed tube. The mixture was then stirred at room temperature for 30 h. The mixture was cooled to -40° C. and then tube was opened. Ethanol was added carefully to terminate the reaction until no gas generated. Water (200 mL) was added and the mixture was adjusted to pH 7 with acetic acid. The resulting solid was filtered to obtain crude product which was purified by column chromatography on silica gel (methylene chloride/methanol at 50:1) to obtain the title compound 0107 as a white solid (718 mg, 77%): LCMS: 287 [M]+; 1H NMR (DMSO-d6) δ 3.68 (s, 3H), 5.31 (s, 2H), 6.06 (s, 2H), 6.59 (d, 1H, J=6.3 Hz), 6.85 (d, 2H, J=9.0 Hz), 7.33 (d, 2H, J=8.4 Hz), 7.64 (d, 1H, J=5.7 Hz), 12.53 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 24h; | 7.a Step 7a. 2-(Benzofuran-5-ylthio)-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-4-amine (Compound 0205-10) A mixture of compound 0204 (1.0 g, 3.5 mmol), 5-iodobenzofuran (1.2 g, 4.92 mmol), neocuproine hydrate (73 mg, 0.35 mmol), CuI (67 mg, 0.35 mmol) and NaO-t-Bu (403 mg, 4.2 mmol) in anhydrous DMF (20 mL) was stirred for 24 h at 110° C. (oil bath) under nitrogen atmosphere. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel (CH2Cl2/MeOH=50/1) to give the title compound 0205-10 as a yellow solid (0.44 g, 31%): LCMS: 403 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 10h;Inert atmosphere; | Method B: 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2-thiol (100 mg, 0.349 mmol), <strong>[5279-32-3]5,6-dibromo-1,3-benzodioxole</strong> (196 mg, 0.698 mmol), Pd2dba3 (16 mg, 1.8×10-2 mmol), Xantphos (21 mg, 3.5×10-2 mmol), and Cs2CO3 (227 mg, 0.698 mmol) were placed in a vial and degassed dioxane (1.2 mL) was added to the mixture. After heating at 100 C. for 10 h, the mixture was diluted with EA, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, MeOH/CH2Cl2, 0 to 10%) to afford the title compound (54 mg, 31%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; iron / 10 h / 40 °C 2.1: potassium hydroxide / ethanol; water / 12 h / Reflux 2.2: 20 °C / pH 7 3.1: sodium amide / ammonia / -78 - 20 °C / Pressure bottle 3.2: pH 7 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With copper(l) iodide; 2.9-dimethyl-1,10-phenanthroline; sodium t-butanolate; In N,N-dimethyl-formamide; at 110℃; for 24h; | General procedure: To 4-amino-l-(4-methoxybenzyl)-lH-imidazo[4,5-c]pyridine-2-thiol (103) (50 mg, 0.174 mmol) was added respective iodine (0.348 mmol), neocuproine hydrate (3.6 mg, 0.0174 mmol), Cul (3.3 mg, 0.0174 mmol), sodium tert-butoxide (25 mg, 0.261 mmol) and lastly DMF (5 mL) and the reaction mixture was stirred at 1 10°C for 24 hours. Then, the solvent was removed under reduced pressure and the crude product was purified by preparatory TLC (CH2Cl2:MeOH-NH3 (7N), 10: 1) to afford desired compounds 104a-c. [0457] 2-((3,5-dichlorophenyl)thio)-l-(4-methoxybenzyl)-lH-imidazo[4,5-c]pyridin-4-amine (104a). Obtained as pale yellow solid 39percent yield. LCMS found m/z 430.97 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; iron / methanol; water / 20 °C / Reflux 2: potassium hydroxide / water; ethanol / Reflux 3: sodium amide; ammonia / 30 h / 20 °C / Sealed tube |