Home Cart 0 Sign in  
X

[ CAS No. 7239-81-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 7239-81-8
Chemical Structure| 7239-81-8
Chemical Structure| 7239-81-8
Structure of 7239-81-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 7239-81-8 ]

Related Doc. of [ 7239-81-8 ]

Alternatived Products of [ 7239-81-8 ]

Product Details of [ 7239-81-8 ]

CAS No. :7239-81-8 MDL No. :MFCD09701424
Formula : C6H5N3S Boiling Point : -
Linear Structure Formula :- InChI Key :SCARFFIFMQUARC-UHFFFAOYSA-N
M.W : 151.19 Pubchem ID :12610114
Synonyms :

Safety of [ 7239-81-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7239-81-8 ]

* 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 [ 7239-81-8 ]

[ 7239-81-8 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 75-15-0 ]
  • [ 54-96-6 ]
  • [ 7239-81-8 ]
YieldReaction ConditionsOperation in experiment
99% In pyridine for 5h; Heating;
92% In ethanol at 80℃; for 4h; 1 Example 1 Synthesis of compound III Weigh 3,4-diaminopyridine(8g, 0.0733mol) in the reaction flask,To it was added 60ml of absolute ethanol in turn,carbon disulfide (15.9ml, 0.264mol),After refluxing at 80 °C for 4 h,The disappearance of starting material was monitored by TLC.The reaction solution was cooled to room temperature,Suction filtration, wash the filter cake with ethyl acetate,After drying, 10.2 g of off-white solid was obtained,Yield: 92.0%.
With potassium hydroxide In lithium hydroxide monohydrate at 70℃;
  • 2
  • [ 54-96-6 ]
  • [ 13037-22-4 ]
  • [ 7239-81-8 ]
YieldReaction ConditionsOperation in experiment
90% In N,N-dimethyl-formamide for 5h; Heating;
  • 4
  • [ 4637-24-5 ]
  • [ 7239-81-8 ]
  • [ 7397-69-5 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile for 0.5h; Heating;
  • 5
  • [ 4637-24-5 ]
  • [ 7239-81-8 ]
  • [ 7297-55-4 ]
  • [ 7321-99-5 ]
  • [ 7321-95-1 ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 10% 3: 15% In acetonitrile for 6.25h; Heating;
YieldReaction ConditionsOperation in experiment
Imidazo<4,5-c>pyridin (II), S;
3,4-Diaminopyridin/EtOH, CS2/EtOH (6h Siedetemp.);
3,4-Diaminopyridin, CS2/Py.;
  • 7
  • 4-bromomethyl-benzene-1,2-diol dibenzoate [ No CAS ]
  • [ 7239-81-8 ]
  • 4-(3H-imidazo[4,5-c]pyridin-2-ylthiomethyl)benzene-1,2-diol dibenzoate (ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform 12 4-(3H-Imidazo[4,5-c]pyridin-2-ylthiomethyl)benzene-1,2-diol dibenzoate (ester) Quarter Hydrate EXAMPLE 12 4-(3H-Imidazo[4,5-c]pyridin-2-ylthiomethyl)benzene-1,2-diol dibenzoate (ester) Quarter Hydrate The synthesis of this compound proceed in the same fashion as in Example 3 using 1.77 g (0.0117 mol) of 2-mercapto-1H- imidazo[4,5-c]pyridine, 0.30 g (0.0129 g atom) of sodium and 4.81 g (0.0117 mol) of 4-bromomethyl-benzene-1,2-diol dibenzoate. Recrystallization of the precipitate from chloroform gave 2.10 g of pure product, m.p. 173°-175° C. Elemental analysis for C27 H19 N3 O4 S. 1/4 H2 O: Calc'd: C, 66.72; H, 4.04; N, 8.65; Found: C, 66.71; H, 3.93; N, 8.43.
  • 8
  • [ 7239-81-8 ]
  • [ 154356-11-3 ]
  • 3-(1H-imidazo[4,5-c]pyridin-2-ylthiomethyl)-benzoic acid phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate 19 3-(1H-Imadazo[4,5-c]pyridin-2-ylthiomethyl)-benzoic acid phenyl ester Quarter Hydrate EXAMPLE 19 3-(1H-Imadazo[4,5-c]pyridin-2-ylthiomethyl)-benzoic acid phenyl ester Quarter Hydrate The synthesis of this compound proceeded in the same fashion as in Example 3 using 6.66 g (0.0441 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine, 1.12 g (0.0485 g atom) of sodium and 14.13 g (0.0485 mol) of 3-(bromomethyl)benzoic acid phenyl ester. Recrystallization of the precipitate from ethyl acetate gave 10.20 g of product, m.p. 129°-132° C. Elemental analysis for C20 H15 N3 O2 S.1/4H2 O; Calc'd: C, 65.64; H, 4.27; N, 11.48; Found: C, 65.75; H, 4.26; N, 11.44.
  • 9
  • [ 73374-11-5 ]
  • [ 7239-81-8 ]
  • 2-[(1H-imidazo[4,5-c]pyridin-2-ylthio)methyl]phenol benzoate (ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
25 2-[(1H-Imidazo[4,5-c]pyridin-2-ylthio)methyl]phenol benzoate (ester) EXAMPLE 25 2-[(1H-Imidazo[4,5-c]pyridin-2-ylthio)methyl]phenol benzoate (ester) The synthesis of this compound proceeded in the same fashion as in Example 3 using 6.79 g (0.045 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine, 1.14 g (0.0495 g atom) of sodium and 13.09 g (0.045 mol) of 2-(bromomethyl)phenyl benzoate. Purification of the crude material (12.75 g) by HPLC gave a product which on recrystallization from ethyl acetate had a m.p. 129°-132° C. Elemental analysis for C20 H15 N3 O2 S: Calc'd: C, 66.47; H, 4.18; N, 11.63; Found: C, 66.25; H, 4.13; N, 11.60.
  • 10
  • [ 40252-11-7 ]
  • [ 7239-81-8 ]
  • 4-[(1H-imidazo[4,5-c]pyridin-2-ylthio)methyl]-phenol benzoate (ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
28 4-[(1H-Imidazo[4,5-c]pyridin-2-ylthio)methyl]-phenol benzoate (ester) EXAMPLE 28 4-[(1H-Imidazo[4,5-c]pyridin-2-ylthio)methyl]-phenol benzoate (ester) The synthesis of this compound proceeded in the same fashion as in Example 15 using 4.17 g (0.028 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine, 0.70 g (0.030 g atom) of sodium, and 8.04 g (0.028 mol) of 4-(bromomethyl)phenyl benzoate. The filtered precipitate (7.90 g) was recrystallized from methylene chloride to give 5.40 g of product, m.p. 171°-174° C. Elemental analysis for C20 H15 N3 O2 S: Calc'd: C, 66.46; H, 4.18; N, 11.62; Found: C, 66.62; H, 4.34; N, 11.46.
  • 11
  • 5-bromomethyl-benzene-1,3-diol dibenzoate [ No CAS ]
  • [ 7239-81-8 ]
  • 5-(3H-imidazo[4,5-c]pyridin-2-ylthiomethyl)benzene-1,3-diol dibenzoate (ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
31 5-(3H-Imidazo[4,5-c]pyridin-2-ylthiomethyl)benzene-1,3-diol dibenzoate (ester) EXAMPLE 31 5-(3H-Imidazo[4,5-c]pyridin-2-ylthiomethyl)benzene-1,3-diol dibenzoate (ester) The synthesis of this compound proceeded in the same fashion as Example 15 using 1.66 g (0.011 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine, 0.28 g (0.012 g atom) of sodium and 4.51 g (0.011 mol) of 5-bromomethyl-benzene-1,3-diol dibenzoate. The crude material (4.2 g) when subjected to HPLC gave pure product (m.p. 209°-212° C.). Elemental analysis for C27 H19 N3 O4 S: Calc'd: C, 67.35; H, 3.98; N, 8.73; Found: C, 67.09; H, 4.04; N, 8.61.
  • 12
  • [ 22071-24-5 ]
  • [ 7239-81-8 ]
  • [3-(1H-imidazo[4,5-c]pyridin-2-ylthiomethyl)-phenyl]-phenyl methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol; water 21 [3-(1H-Imidazo[4,5-c]pyridin-2-ylthiomethyl)-phenyl]-phenyl methanone Quarter Hydrate EXAMPLE 21 [3-(1H-Imidazo[4,5-c]pyridin-2-ylthiomethyl)-phenyl]-phenyl methanone Quarter Hydrate To a solution of 0.46 g (0.02 g atom) of sodium in 120 mL of methanol was added 2.74 g (0.018 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring at room temperature for 30 minutes, 5.0 g (0.018 mol) of 3-bromomethyl-benzophenone was added portionwise. The reaction mixture was stirred overnight at room temperature and was then evaporated to dryness in a rotary evaporator. Water (75 mL) was added to the residue and the resulting material was filtered. Purification by HPLC gave a product which upon recrystallization from ethanol amounted to 9.2 g (m.p. 149°-151° C.). Elemental analysis for C20 H15 N3 OS.1/4 H2 O. Calc'd: C, 68.65; H, 4.47; N, 12.01; Found: C, 68.34; H, 4.54; N, 12.04.
  • 13
  • [ 154356-08-8 ]
  • [ 7239-81-8 ]
  • 3-methoxybenzoic acid 3-(1H-imidazo[4,5-c]pyridin-2-ylthiomethyl)-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium In <i>N</i>-methyl-acetamide; methanol 15 3-Methoxybenzoic acid 3-(1H-imidazo[4,5-c]pyridin-2-ylthiomethyl)-phenyl ester Quarter Hydrate EXAMPLE 15 3-Methoxybenzoic acid 3-(1H-imidazo[4,5-c]pyridin-2-ylthiomethyl)-phenyl ester Quarter Hydrate To a solution of 1.01 g (0.044 g atom) of sodium in 225 mL of methanol was added 6.04 g (0.04 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring for 20 minutes at room temperature, the reaction mixture was evaporated to dryness in a rotary evaporator. To the residue was added 150 mL of dimethylformamide followed by the portionwise addition of 12.85 g (0.04 mol) of 3-methoxy-benzoic acid 3-bromomethyl-phenyl ester. The reaction mixture was stirred overnight at room temperature and was then poured into 500 mL of chilled water. The product was removed by filtration and amounted to 9.66 g. An analytical sample (m.p. 149°-151° C.) was obtained by recrystallization from ethyl acetate. Elemental analysis for C21 H17 N3 O3 S.1/4 H2 O: Calc'd: C, 63.70; H, 4.46; N, 10.61; Found: C, 63.72; H, 4.37; N, 10.77.
  • 14
  • [ 7239-81-8 ]
  • [ 824-98-6 ]
  • [ 134217-26-8 ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol; water; N,N-dimethyl-formamide 2 2-[[(3-Methoxyphenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine EXAMPLE 2 2-[[(3-Methoxyphenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine To a solution containing 3.45 g (0.15 g atom) of sodium dissolved in 800 mL of methanol was added 22.65 g (0.15 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. The reaction mixture was stirred for 1/2 hour at room temperature. The solvent was removed in a rotary evaporator and to the residue was added 465 mL of DMF. 3-Methoxybenzyl chloride (23.49 g, 0.15 mol) was then added dropwise and the reaction mixture was stirred overnight at room temperature. The reaction mixture was poured into approximately 1800 mL of water and allowed to cool for several hours in an ice bath. The product was removed by filtration and amounted to 28.3 g. Recrystallization from ethyl acetate gave 18.6 g of product. An analytical sample (m.p. 133°-136° C.) was obtained by recrystallization from ethanol. Anal. Calcd. for C14 H13 N3 OS: C, 61.97; H, 4.83; N, 15.49. Found: C, 61.91; H, 4.81; N, 15.48.
  • 15
  • [ 54-96-6 ]
  • [ 7239-81-8 ]
YieldReaction ConditionsOperation in experiment
With carbon disulfide In ethanol 1 2-Mercapto-1H-imidazo[4,5-c]pyridine EXAMPLE 1 2-Mercapto-1H-imidazo[4,5-c]pyridine A mixture of 25 g (0.23 mol) of 3,4-diaminopyridine in 750 mL of ethanol containing 50 mL (63.2 g, 0.83 mol) of carbon disulfide was heated under reflux for 5 hours. The reaction mixture was allowed to cool to room temperature and the beige precipitate which had formed was collected by filtration and allowed to air dry overnight. The product amounted to 33.5 g, m.p. >320° C. Ref. G. B. Barlin, J. Chem. Soc. (B) 285 (1966).
With carbon disulfide In ethanol 1 2-Mercapto-1H-imidazo[4,5-c]pyridine EXAMPLE 1 2-Mercapto-1H-imidazo[4,5-c]pyridine A mixture of 25 g (0.23 mol) of 3,4-diaminopyridine in 750 mL of ethanol containing 50 mL (63.2 g), 0.83 mol) of carbon disulfide was heated under reflux for 5 hours. The reaction mixture was allowed to cool to room temperature and the beige precipitate which had formed was collected by filtration and allowed to air dry overnight. The product amounted to 33.5 g, m.p.>320° C. Ref. G. B. Barlin, J. Chem. Soc (B) 285 (1966).
  • 16
  • [ 38661-81-3 ]
  • [ 7239-81-8 ]
  • [ 135903-94-5 ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol; N,N-dimethyl-formamide 13 2-[(2-Phenylethyl)thio]-1H-imidazo[4,5-c]pyridine EXAMPLE 13 2-[(2-Phenylethyl)thio]-1H-imidazo[4,5-c]pyridine To a solution of 0.17 g (0.0074 g atom) of sodium in 35 mL of methanol was added 1.0 g (0.0066 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring the reaction for 25 minutes at room temperature, the reaction mixture was evaporated to dryness in a rotary evaporator. To the residue was added 20 mL of DMF. To the resulting solution was added dropwise, 1.22 g (0.0066 mol) of 2-(bromoethyl)benzene in 3 mL of DMF. The reaction mixture was stirred overnight at room temperature and was then poured into 100 mL of chilled water. There was obtained 1.0 g of product. An analytical sample (m.p. 164°-166° C.) was prepared by recrystallization from ethanol. Anal. Calcd. for C14 H13 N3 S: C, 65.85; H, 5.13; N, 16.46 Found: C, 66.04; H, 5.23; N, 16.06.
  • 17
  • [ 100-44-7 ]
  • [ 33513-42-7 ]
  • [ 7239-81-8 ]
  • [ 135903-92-3 ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol; water 11 2-[[(Phenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine EXAMPLE 11 2-[[(Phenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine To a solution of 1.26 g (0.055 g atom) of sodium in 300 mL of methanol was added 7.56 g (0.05 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine with stirring. After 20 minutes, the reaction mixture was evaporated to dryness in a rotary evaporator. Dimethyl formamide (200 mL) was added to the residue. To the resulting solution was added dropwise 6.33 g (0.05 mol) of benzylchloride. The reaction mixture was stirred for 5 hours at room temperature and was then poured into 1500 mL of water. The product was removed by filtration and amounted to 9.5 g, m.p. 175°-177° C. The product was triturated with hot ethyl acetate and refiltered. The product amounted to 8.11 g, m.p. 175°-177° C. A portion recrystallized from ethyl acetate gave the analytical sample (m.p. 175°-177° C.). Anal. Calcd. for C13 H11 N3 S: C, 64.70; H, 4.59; N, 17.41. Found: C, 64.55; H, 4.62; N, 17.12.
  • 18
  • p- toluenesulfonate ester [ No CAS ]
  • [ 5020-41-7 ]
  • [ 7239-81-8 ]
  • 2-[[(3-Methoxyphenyl)ethyl]thio]-1H-imidazo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium; In methanol; N,N-dimethyl-formamide; EXAMPLE 16 2-[[(3-Methoxyphenyl)ethyl]thio]-1H-imidazo[4,5-c]pyridine To a solution of 0.81 g (0.035 g atom) of sodium in 170 mL of methanol was added 4.83 g (0.032 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring for 25 minutes, the methanol was removed in a rotary evaporator and to the residue was added 100 mL of DMF. The residue dissolved after heating for a few minutes. The reaction mixture was allowed to cool to room temperature and 9.79 g (0.032 mol) of 3-methoxyphenethanol, p- toluenesulfonate ester in 5 mL of DMF was slowly added dropwise. The reaction mixture was allowed to stir at room temperature overnight and then was poured into 725 mL of chilled water. The reaction mixture was extracted with chloroform (3*200 mL). The combined organic phase was dried over magnesium sulfate, filtered and the filtrate was evaporated to dryness in a rotary evaporator. The crude product amounted to 12.6 g which was used directly in the next step.
  • 19
  • [ 102-47-6 ]
  • [ 7239-81-8 ]
  • [ 135903-87-6 ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol; N,N-dimethyl-formamide 5 2-[[(3,4-Dichlorophenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine EXAMPLE 5 2-[[(3,4-Dichlorophenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine To a solution of 0.34 g (0.015 g atom) of sodium in 70 mL of methanol was added 2.0 g (0.013 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. The reaction mixture was stirred at room temperature for 20 minutes and was evaporated to dryness in a rotary evaporator. To the residue was added 40 mL of DMF followed by the dropwise addition of 2.54 g (0.013 mol) of α,3,4-trichlorotoluene in 3 mL of DMF. The reaction mixture was stirred overnight at room temperature and was then poured into 400 mL of chilled water. The reaction mixture was extracted with chloroform (3*150 mL). The organic phases were combined and dried over magnesium sulfate. The solution was filtered and the filtrate was evaporated to dryness in a rotary evaporator. There was obtained 2.66 g of product. An analytical sample (m.p. 190°-193° C.) was obtained by recrystallization from acetonitrile. Anal. Calcd. for C13 H9 Cl2 N3 S: C, 50.34; H, 2.92; N, 13.55. Found: C, 50.41; H, 2.72; N, 13.46.
  • 20
  • [ 7239-81-8 ]
  • [ 705-29-3 ]
  • 2-[[[3-(Trifluoromethyl)phenyl]methyl]thio]-1H-imidazo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide 7 2-[[[3-(Trifluoromethyl)phenyl]methyl]thio]-1H-imidazo[4,5-c]pyridine EXAMPLE 7 2-[[[3-(Trifluoromethyl)phenyl]methyl]thio]-1H-imidazo[4,5-c]pyridine To a solution of 0.15 g (0.0065 g atom) of sodium in 35 mL of methanol was added 1.0 g (0.0066 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring for 15 minutes at room temperature, the methanol was removed in a rotary evaporator. The residue was dissolved in 20 mL of DMF and 1.28 g (0.0066 mol) of α'-chloro-α,α,α-trifluoro-m-xylene in 2 mL of DMF was added dropwise to the reaction solution. The reaction mixture was stirred at room temperature overnight and was then poured into 150 mL of ice water. The product which crystallized was collected and amounted to 1.61 g. An analytical sample (m.p. 148°-150° C.) was obtained by recrystallization from acetonitrile. Anal. Calcd. for C14 H10 F3 N3 S: C, 54.36; H, 3.26; N, 13.59. Found: C, 54.45; H, 3.21; N, 13.50.
  • 21
  • [ 55117-15-2 ]
  • [ 7239-81-8 ]
  • 2-[[(2-Chloro-6-fluorophenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium In ethanol; N,N-dimethyl-formamide 9 2-[[(2-Chloro-6-fluorophenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine EXAMPLE 9 2-[[(2-Chloro-6-fluorophenyl)methyl]thio]-1H-imidazo[4,5-c]pyridine To a solution of 0.34 g (0.015 g atom) of sodium in 70 mL of ethanol was added 2.0 g (0.013 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring at room temperature for 25 minutes, the reaction mixture was evaporated to dryness in a rotary evaporator. To the residue was added 40 mL of DMF. To the resulting solution was added dropwise 2.33 g (0.013 mol) of 2-chloro-6-fluorobenzyl chloride in 3 mL of DMF. The reaction mixture was stirred overnight at room temperature and was then poured into 400 mL of chilled water. The precipitate that formed was collected by filtration and amounted to 3.11 g. An analytical sample (m.p. 224°-226° C.) was obtained by recrystallization from ethanol. Anal. Calcd. for C13 H9 ClFN3 S: C, 53.15; H, 3.09; N, 14.30. Found: C, 53.29; H, 3.30; N, 13.95.
  • 22
  • [ 7239-81-8 ]
  • [ 1353678-04-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 3 h 2: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10 h / 0 °C 3: N,N-dimethyl-formamide / 1 h / 20 °C 4: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 120 °C / Microwave irradiation; Sealed tube 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 100 °C / Microwave irradiation; Sealed tube
  • 23
  • [ 7239-81-8 ]
  • [ 1353678-05-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 3 h 2: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10 h / 0 °C
  • 24
  • [ 7239-81-8 ]
  • [ 1353678-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 3 h 2: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10 h / 0 °C 3: N,N-dimethyl-formamide / 1 h / 20 °C
  • 25
  • [ 7239-81-8 ]
  • [ 1353679-50-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 3 h 2: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10 h / 0 °C 3: N,N-dimethyl-formamide / 1 h / 20 °C 4: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 120 °C / Microwave irradiation; Sealed tube
  • 26
  • [ 7239-81-8 ]
  • [ 74-88-4 ]
  • [ 7397-69-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone for 3h; 115.115b 115b) 2-(methylsulfanyl)-1H-imidazo[4,5-c]pyridine To a solution of 1H-imidazo[4,5-c]pyridine-2-thiol (4 g) in acetone (50 ml) were added potassium carbonate (11 g) and MeI (1.8 ml). After stirring for 3 h, the mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 10%-70% EtOAc in hexane) to give 2-(methylsulfanyl)-1H-imidazo[4,5-c]pyridine (4.07 g) as a yellow solid.MS (API+): [M+H]+166.0.1H NMR (300 MHz, DMSO-d6) δ 2.72 (3H, s), 7.42-7.52 (1H, m), 8.09-8.27 (1H, m), 8.77 (1H, s)
  • 27
  • [ 75-15-0 ]
  • [ 54-96-6 ]
  • [ 7239-81-8 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20 - 40℃; for 10h; 115.115a Example 1151-ethyl-3-[4-(3H-imidazo[4,5-c]pyridin-2-yloxy)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 115a) 1H-imidazo[4,5-c]pyridine-2-thiol To a solution of pyridine-3,4-diamine (5 g) in EtOH (80 ml) was added carbon disulfide (10 mL) at room temperature. The mixture was stirred at 40° C. under a dry atmosphere (CaCl2 tube) for 10 h. The mixture was cooled to room temperature. The resulting white solid was collected by filtration and washed with ether to give 1H-imidazo[4,5-c]pyridine-2-thiol (6.1 g) as a white solid.MS (API+): [M+H]+ 152.01H NMR (300 MHz, DMSO-d6) δ 7.17 (1H, d, J=5.29 Hz), 8.25 (1H, d, J=5.67 Hz), 8.38 (1H, s), 12.87 (2H, br. s.).
  • 28
  • [ 75-15-0 ]
  • [ 54-96-6 ]
  • [ 7239-81-8 ]
YieldReaction ConditionsOperation in experiment
66.4% Stage #1: carbon disulfide With water; potassium hydroxide In ethanol at 20℃; for 0.25h; Stage #2: 3,4-diaminopyridine In ethanol at 130℃; for 0.25h; Microwave irradiation; 19 Example 19: Preparation of MMAE compounds comprising an activated hindered disulfide Carbon disulfide (191 mg, 2.52mmol) was added to a mixture of KOH (141 mg, 2.52 mmol) in EtOH (4.0 mL) and water (1.0 mL). The reaction mixture was stirred at 20 °C for 15 mm. Then compound 3 (250 mg, 2.29 mmol) was added. The reaction mixture was heated undermicrowave irradiation at 130 °C for 15 mm and cooled to r.t. The reaction mixture was diluted with H20 (10 mL), adjusted to pH = 5 with HOAc, and cooled to 0 °C. The solid was filtered and dried under reduced pressure to give compound 2 (230 mg, 66.4%) as a white solid. ‘H NMR (400 MHz, DMSO-d6) 5 12.87-12.84 (m, 2H), 8.36 (s, 1H), 8.23 (d, J= 5.2 Hz, 1H), 7.15 (d,J=5.2Hz, 1H).
With potassium hydroxide In ethanol at 90℃; 3-1.1 Step 1. 3H-imidazo[4,5-c]pyridine-2-thiol A solution of pyridine-3, 4-diamine (1.00 g, 9.16 mmol), carbon disulfide (14.00 g, 183.9 mmol), and potassium hydroxide (1.56 g, 27.8 mmol) in ethanol (25 mL) stirred overnight at 90 °C. The resulting solution was diluted with 50 mL of water, and the pH value of the solution was adjusted to 6 with 6 M aqueous HC1 solution. The solids were collected by filtration and dried to give 3H-imidazo[4,5-c]pyridine-2-thiol (500 mg) as an off-white solid which was used without purification. MS: (ESI, m/z): 152 [M+H]+.
  • 29
  • [ 1681-37-4 ]
  • [ 7239-81-8 ]
  • 30
  • [ 7239-81-8 ]
  • [ 518-28-5 ]
  • C28H25N3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid Cooling with ice; 21.1 Example 21 Synthesis and Purification of 4β-S-(1H-Imidazo[4,5-B]pyridine-2)-podophyllotoxin (Compound 21) (1) Synthesis of 4β-S-(1H-imidazo[4,5-B]pyridine-2)-podophyllotoxin: 414 mg (1 mmol) of scorpionToxin, 151 mg (1 mmol) of 1H-imidazo[4,5-B]pyridine-2-thiol, dried under vacuum for 1 h, under ice-cooling conditions, 15 mLFluoroacetic acid was used as a solvent, and the mixture was vacuum-stirred for 1 to 3 hours, and chloroform acetone was used as a developing solvent to detect the reaction end point. Add the reaction system to 20In ~50 volumes of deionized water, the filter cake was collected by filtration and washed to obtain a crude product.
  • 31
  • [ 6559-91-7 ]
  • [ 7239-81-8 ]
  • 4β-S-(5-azabenzimidazole-2)-4-deoxy-4'-demethylepipodophyllotoxin [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 3h; 5.3 Chemical synthesis General procedure: A mixture of 4′-demethylepipodophyllotoxin (DMEP) (400mg 1mmol) and SH-containing building blocks in dichloromethane (15mL) at 0°C was mixed with 1mL of TFA as the catalyst. After stirring the reaction mixture for 2-3hat room temperature and maximal conversion was reached (3h, monitored by TLC), the resultant mixture was washed with saturated NaHCO3 (20mL×2) and extracted with CH2Cl2 (45mL×2). The organic layer was dried over MgSO4, and the solvent was evaporated to give a crude residue, which was purified by flash column chromatography (petroleum ether: dichloromethane: ethyl acetate, 3:2:1) to afford the target compounds. The purity of compounds was determined by HPLC with a thermo-C18 (250mm×4.6mm, 5μm) column as the stationary phase and methanol-water (35:65) as the mobile phase at ambient temperature and a flow rate of 2.0mL/min.
With trifluoroacetic acid Cooling with ice; 22.1 Example 22 Synthesis and Purification of 4β-S-(1H-Imidazo[4,5-B]pyridine-2)-4'-demethylepipodophyllotoxin (Compound 22) (1) Synthesis of 4β-S-(1H-imidazo[4,5-B]pyridine-2)-4'-demethylepipodophyllotoxin: 400mg(1 mmol) of 4'-demethylepipodophyllotoxin, 151 mg (1 mmol) of 1H-imidazo[4,5-B]pyridine-2-thiol, dried under vacuum1h, under ice bath conditions with 15mL of trifluoroacetic acid as solvent, vacuum stirring for 1-3h, using chloroform acetone as developing agent, detection reactionend. Adding the reaction system to 20-50 times volume of deionized water, collecting the filter cake by filtration, drying and dryingObject.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 7239-81-8 ]

Amides

Chemical Structure| 30162-37-9

[ 30162-37-9 ]

1-(Pyridin-3-yl)thiourea

Similarity: 0.86